Rotenone supplier | CasNO.83-79-4

Name
ROTENONE
EINECS 201-501-9
CAS No. 83-79-4
Article Data16
CAS DataBase
Density 1.271 g/cm³
Solubility 0.2 mg/L at 20 °C in water
Melting Point 159-164 °C
Formula C₂₃H₂₂O₆
Boiling Point 559.8 °C at 760 mmHg
Molecular Weight 394.424
Flash Point 244.6 °C
Transport Information UN 2811 6.1/PG 3
Appearance white or off-white powder
Safety 22-24/25-36-45-60-61
Risk Codes 25-36/37/38-50/53
Molecular Structure
Hazard Symbols N,T
Synonyms Rotenone(7CI);[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one,1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, [2R-(2a,6aa,12aa)]-;[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aaH)-one, 1,2,12,12aa-tetrahydro-2a-isopropenyl-8,9-dimethoxy-(8CI);(-)-Rotenone;(-)-cis-Rotenone;5'b-Rotenone;Cube-Pulver;Dactinol;Deril;Derrin;Derris;Derris (insecticide);Dri-kil;Liquid Derris;NSC 26258;NSC 8505;Nicouline;Noxfish;Paraderil;Rotenone;
PSA 63.22000
LogP 3.70330

Synthetic route

: 23355-70-6
(6aS,12aS,5'R)-rotenone enol acetate

: 83-79-4
rotenone

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating;	83%

: 186581-53-3, 908094-01-9
diazomethane

: 34487-52-0
(2R,6aS,12aS)-8-hydroxy-9-methoxy-2-(prop-1-en-2-yl)-1,2,12,12a- tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

: 83-79-4
rotenone

Conditions

Conditions	Yield
In diethyl ether	59%

: 30462-22-7
2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol

A: 83-79-4
rotenone

B: 549-22-4
Isorotenone

Conditions

Conditions	Yield
With Burgess Reagent In toluene for 0.5h; Reflux;	A 50% B 13%
With Burgess Reagent In toluene for 0.5h; Inert atmosphere; Reflux;	A 50% B 13%

: 30462-22-7
2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol

: 83-79-4
rotenone

Conditions

Conditions	Yield
With pyridine; thionyl chloride at 0℃; for 0.5h;	40%

: 123000-20-4
(6aS,12aR,5'R)-(trans)-(+)-rotenone

: 83-79-4
rotenone

Conditions

Conditions	Yield
With hydrogenchloride In methanol; chloroform for 2h;

: 123000-19-1
(6aR,12aS,5'R)-rotenone

: 83-79-4
rotenone

Conditions

Conditions	Yield
With hydrogenchloride In methanol; chloroform
With hydrogenchloride In methanol; chloroform epimerisation;

: 509-96-6
12a-hydroxyrotenone

: 83-79-4
rotenone

Conditions

Conditions	Yield
With acetic acid; zinc(II) chloride; zinc In water at 100℃; for 2.5h;	20 mg

: 3466-09-9
6a,12a-dehydrorotenone

: 83-79-4
rotenone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 31 mg / diisobutyaluminium hydride / toluene; tetrahydrofuran / 1 h / -78 °C 2: aq. HCl / methanol; CHCl3 / 2 h View Scheme
Multi-step reaction with 2 steps 1: di-isobutylaluminium hydride 2: hydrogen chloride / methanol; CHCl3 / epimerisation View Scheme

: 15130-81-1
(6aS,12aS,5′R)-rotenone-6′-norketone

A: 83-79-4
rotenone

B aqueous-alcoholic KOH-solution: aqueous-alcoholic KOH-solution

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 50 percent / conc. H2SO4 / 3 h / Heating 2: 1.) n-BuLi / 1.) THF, 35 deg C, 5 min, 2.) THF, 1 h 3: 83 percent / conc. HCl / methanol / 2 h / Heating View Scheme

: 23295-59-2, 23295-65-0
rotenone 6'-norketone enol acetate

A: 83-79-4
rotenone

B aqueous-alcoholic KOH-solution: aqueous-alcoholic KOH-solution

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, 35 deg C, 5 min, 2.) THF, 1 h 2: 83 percent / conc. HCl / methanol / 2 h / Heating View Scheme

: C11H14F2O2

: 83-79-4
rotenone

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C 2.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 3.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 3.2: 1.5 h / -78 - -30 °C 4.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 5.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 6.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 8.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 9.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 10.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 11.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 12.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 12.2: 1.5 h / 50 °C 13.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 13 steps
1.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C
2.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C
3.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
3.2: 1.5 h / -78 - -30 °C
4.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
5.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
6.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
8.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
9.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
10.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
11.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
12.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
12.2: 1.5 h / 50 °C
13.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme

: C11H14F2O2

A: 83-79-4
rotenone

B: 549-22-4
Isorotenone

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C 2.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 3.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 3.2: 1.5 h / -78 - -30 °C 4.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 5.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 6.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 8.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 9.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 10.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 11.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 12.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 12.2: 1.5 h / 50 °C 13.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme

Yield

Multi-step reaction with 13 steps
1.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C
2.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C
3.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
3.2: 1.5 h / -78 - -30 °C
4.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
5.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
6.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
8.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
9.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
10.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
11.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
12.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
12.2: 1.5 h / 50 °C
13.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme

: C11H13FO2

: 83-79-4
rotenone

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 2.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 2.2: 1.5 h / -78 - -30 °C 3.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 4.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 5.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 7.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 8.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 9.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 10.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 11.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 11.2: 1.5 h / 50 °C 12.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 12 steps
1.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C
2.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
2.2: 1.5 h / -78 - -30 °C
3.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
4.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
5.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
7.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
8.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
9.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
10.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
11.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
11.2: 1.5 h / 50 °C
12.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme

: C11H13FO2

A: 83-79-4
rotenone

B: 549-22-4
Isorotenone

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 2.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 2.2: 1.5 h / -78 - -30 °C 3.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 4.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 5.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 7.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 8.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 9.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 10.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 11.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 11.2: 1.5 h / 50 °C 12.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme

Yield

Multi-step reaction with 12 steps
1.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C
2.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
2.2: 1.5 h / -78 - -30 °C
3.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
4.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
5.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
7.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
8.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
9.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
10.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
11.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
11.2: 1.5 h / 50 °C
12.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme

: C13H17FO3

: 83-79-4
rotenone

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 1.2: 1.5 h / -78 - -30 °C 2.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 3.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 4.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 6.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 7.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 8.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 9.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 10.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 10.2: 1.5 h / 50 °C 11.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 11 steps
1.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
1.2: 1.5 h / -78 - -30 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
3.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
4.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
6.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
7.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
8.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
9.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
10.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
10.2: 1.5 h / 50 °C
11.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme

: C13H17FO3

A: 83-79-4
rotenone

B: 549-22-4
Isorotenone

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 1.2: 1.5 h / -78 - -30 °C 2.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 3.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 4.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 6.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 7.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 8.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 9.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 10.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 10.2: 1.5 h / 50 °C 11.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme

Yield

Multi-step reaction with 11 steps
1.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
1.2: 1.5 h / -78 - -30 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
3.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
4.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
6.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
7.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
8.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
9.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
10.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
10.2: 1.5 h / 50 °C
11.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme

: 372-18-9
1,3-Difluorobenzene

: 83-79-4
rotenone

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1.42 h / -78 °C 1.2: 2 h / 20 °C 2.1: potassium osmate; potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tert-butyl alcohol; water / 120 h / 0 - 20 °C 3.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 5.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 5.2: 1.5 h / -78 - -30 °C 6.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 7.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 8.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 10.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 11.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 12.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 13.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 14.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 14.2: 1.5 h / 50 °C 15.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 15 steps
1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1.42 h / -78 °C
1.2: 2 h / 20 °C
2.1: potassium osmate; potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tert-butyl alcohol; water / 120 h / 0 - 20 °C
3.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C
4.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C
5.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
5.2: 1.5 h / -78 - -30 °C
6.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
7.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
8.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
10.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
11.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
12.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
13.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
14.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
14.2: 1.5 h / 50 °C
15.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme

: 372-18-9
1,3-Difluorobenzene

A: 83-79-4
rotenone

B: 549-22-4
Isorotenone

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1.42 h / -78 °C 1.2: 2 h / 20 °C 2.1: potassium osmate; potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tert-butyl alcohol; water / 120 h / 0 - 20 °C 3.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 5.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 5.2: 1.5 h / -78 - -30 °C 6.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 7.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 8.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 10.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 11.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 12.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 13.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 14.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 14.2: 1.5 h / 50 °C 15.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme

Yield

Multi-step reaction with 15 steps
1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1.42 h / -78 °C
1.2: 2 h / 20 °C
2.1: potassium osmate; potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tert-butyl alcohol; water / 120 h / 0 - 20 °C
3.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C
4.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C
5.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C
5.2: 1.5 h / -78 - -30 °C
6.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
7.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
8.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
10.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
11.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
12.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
13.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
14.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
14.2: 1.5 h / 50 °C
15.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme

: C31H44F2O8Si

: 83-79-4
rotenone

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 2.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 3.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 5.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 6.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 7.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 8.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 9.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 9.2: 1.5 h / 50 °C 10.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 10 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
2.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
3.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
5.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
6.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
7.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
8.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
9.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
9.2: 1.5 h / 50 °C
10.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme

: C31H44F2O8Si

A: 83-79-4
rotenone

B: 549-22-4
Isorotenone

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 2.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 3.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 5.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 6.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 7.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 8.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 9.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 9.2: 1.5 h / 50 °C 10.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme
Multi-step reaction with 10 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 4.1: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux 5.1: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere 6.1: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere 7.1: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C 8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere 9.1: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere 10.1: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux View Scheme

Yield

Multi-step reaction with 10 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C
2.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
3.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
5.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
6.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
7.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
8.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
9.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
9.2: 1.5 h / 50 °C
10.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme

Multi-step reaction with 10 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
1.2: 0.5 h / 20 °C / Inert atmosphere
2.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
4.1: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux
5.1: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere
6.1: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere
7.1: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere
9.1: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere
10.1: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux
View Scheme

: C31H46F2O8Si

: 83-79-4
rotenone

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 4.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 5.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 6.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 7.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 7.2: 1.5 h / 50 °C 8.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 8 steps
1.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
3.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
4.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
5.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
6.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
7.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
7.2: 1.5 h / 50 °C
8.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme

: C31H46F2O8Si

A: 83-79-4
rotenone

B: 549-22-4
Isorotenone

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 4.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 5.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 6.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 7.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 7.2: 1.5 h / 50 °C 8.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme
Multi-step reaction with 9 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux 4: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere 5: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere 6: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C 7: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere 8: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere 9: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux View Scheme

Yield

Multi-step reaction with 8 steps
1.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
3.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
4.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
5.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
6.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
7.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
7.2: 1.5 h / 50 °C
8.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme

Multi-step reaction with 9 steps
1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
3: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux
4: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere
5: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere
6: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C
7: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere
8: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere
9: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux
View Scheme

: C31H44F2O8Si

: 83-79-4
rotenone

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 2.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 4.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 5.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 6.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 7.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 8.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 8.2: 1.5 h / 50 °C 9.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
2.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
4.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
5.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
6.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
7.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
8.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
8.2: 1.5 h / 50 °C
9.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme

: C31H44F2O8Si

A: 83-79-4
rotenone

B: 549-22-4
Isorotenone

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 2.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 4.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 5.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 6.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 7.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 8.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 8.2: 1.5 h / 50 °C 9.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme

Yield

Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C
2.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
4.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
5.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
6.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
7.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
8.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
8.2: 1.5 h / 50 °C
9.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme

: C39H52F2O9Si

: 83-79-4
rotenone

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 2.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 3.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 4.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 5.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 6.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 6.2: 1.5 h / 50 °C 7.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
2.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
3.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
4.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
5.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
6.2: 1.5 h / 50 °C
7.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme

: C39H52F2O9Si

A: 83-79-4
rotenone

B: 549-22-4
Isorotenone

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 2.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 3.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 4.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 5.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 6.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 6.2: 1.5 h / 50 °C 7.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme
Multi-step reaction with 8 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 2: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux 3: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere 4: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere 5: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C 6: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere 7: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere 8: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux View Scheme

Yield

Multi-step reaction with 7 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
2.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
3.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
4.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
5.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
6.2: 1.5 h / 50 °C
7.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme

Multi-step reaction with 8 steps
1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
2: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux
3: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere
4: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere
5: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C
6: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere
7: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere
8: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux
View Scheme

: C33H38F2O9

: 83-79-4
rotenone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 2.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 3.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 4.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 5.2: 1.5 h / 50 °C 6.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
2.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
3.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
4.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
5.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
5.2: 1.5 h / 50 °C
6.1: pyridine; thionyl chloride / 0.5 h / 0 °C
View Scheme

: C33H38F2O9

A: 83-79-4
rotenone

B: 549-22-4
Isorotenone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 2.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 3.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 4.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 5.2: 1.5 h / 50 °C 6.1: Burgess Reagent / toluene / 0.5 h / Reflux View Scheme
Multi-step reaction with 7 steps 1: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux 2: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere 3: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere 4: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C 5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere 6: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere 7: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux View Scheme

Yield

Multi-step reaction with 6 steps
1.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux
2.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C
3.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C
4.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C
5.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C
5.2: 1.5 h / 50 °C
6.1: Burgess Reagent / toluene / 0.5 h / Reflux
View Scheme

Multi-step reaction with 7 steps
1: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine / toluene / 2 h / Inert atmosphere; Reflux
2: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether; dichloromethane / 0.33 h / 0 °C / Inert atmosphere
3: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 2 h / 80 °C / Inert atmosphere
4: 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran; tert-butyl alcohol; water / 3 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere
6: hydrogenchloride / methanol / 1.5 h / 50 °C / Inert atmosphere
7: Burgess Reagent / toluene / 0.5 h / Inert atmosphere; Reflux
View Scheme

: 870-63-3
prenyl bromide

: 83-79-4
rotenone

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1.42 h / -78 °C 1.2: 2 h / 20 °C 2.1: potassium osmate; potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / tert-butyl alcohol; water / 120 h / 0 - 20 °C 3.1: sodium hydride / hexane; mineral oil; N,N-dimethyl-formamide / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C 5.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / hexane; toluene; diethyl ether; cyclohexane / 1 h / -78 °C 5.2: 1.5 h / -78 - -30 °C 6.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / 0 °C 7.1: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C 8.1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 10.1: bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; potassium tert-butylate / toluene / 2 h / Reflux 11.1: aluminum (III) chloride; lithium aluminium tetrahydride / dichloromethane; toluene; diethyl ether / 0.33 h / 0 °C 12.1: sodium hydride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 15-crown-5 / toluene / 2 h / 80 °C 13.1: palladium 10% on activated carbon; hydrogen / tert-butyl alcohol; water / 15 h / 20 °C 14.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C 14.2: 1.5 h / 50 °C 15.1: pyridine; thionyl chloride / 0.5 h / 0 °C View Scheme

Yield

: 83-79-4
rotenone

: 6659-45-6
2R,6aS,12aS-2-isopropyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In dichloromethane at 20℃;	98%
With hydrogen; palladium on activated charcoal In ethyl acetate Ambient temperature;	94%
With hydrogen; palladium on activated charcoal In acetone	90%

: 83-79-4
rotenone

: (2R,6aR,12aS)-8,9-dimethoxy-2(prop-1-en-2-yl)-1,2,6,6a,12,12a- hexahydrochromeno[3,4-b]furo[2,3-h]chromen-6-ol

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 50℃; for 2h;	98%
With sodium tetrahydroborate In methanol at 0℃; for 3h;	95%
Multi-step reaction with 2 steps 1: two-dimensional iron(II) coordination polymer based on a divergent 4'-(4-diphenylamino)phenyl-4,2';6',4''-terpyridine ligand; potassium tert-butylate / tetrahydrofuran / 4 h / 20 °C / Green chemistry 2: silica gel / ethyl acetate; hexane / 20 °C View Scheme
With sodium tetrahydroborate In methanol at 0 - 20℃; for 2h;

: S-(trifluoromethyl)thianthrenium triflate

: 83-79-4
rotenone

: C24H23F3O6

Conditions

Conditions	Yield
With caesium carbonate; Benzene-1,2-dithiol In 1,4-dioxane at 10℃; for 7h; Inert atmosphere; Glovebox;	96%

: 83-79-4
rotenone

: 88390-15-2
(6aS,12S,12aR,5′R)-12-deoxo-12-hydroxyrotenone

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 2h; Inert atmosphere;	92%
With sodium tetrahydroborate In methanol	85%
With lithium aluminium tetrahydride Reduction;
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Reduction; Heating;

: 421-83-0
trifluoromethane sulfonyl chloride

: 83-79-4
rotenone

: (2R,6aS,12aS)-2-(2-chloro-4,4,4-trifluorobutan-2-yl)-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate; tris(1,10-phenanthroline)ruthenium(II) dichloride In dichloromethane at 25℃; for 15h; Inert atmosphere; Irradiation; regioselective reaction;	92%
With dipotassium hydrogenphosphate; tris(1,10-phenanthroline)ruthenium(II) dichloride In dichloromethane at 25℃; for 15h; Photolysis; regioselective reaction;	92%
With 2,4,6-trimethyl-pyridine; [Hf6(μ3-O)4(mu3-OH)4(formato)5.9(eosinato Y)0.1(4'-(4-carboxylatophenyl)[2,2':6',2''-terpyridine]-5,5''-dicarboxylato-Fe(OTf)2)2] In acetonitrile at 20℃; for 2h; Catalytic behavior; Inert atmosphere; Schlenk technique; Irradiation;	70%

: 83-79-4
rotenone

: 3276-14-0, 112838-10-5, 112838-11-6, 112838-12-7
(2R,6aR,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one oxime

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol for 10h; Reflux;	91%
With hydroxylamine hydrochloride; sodium acetate In ethanol for 18h; Reflux;	74%
With pyridine; hydroxylamine hydrochloride	70%
With hydroxylamine

: 83-79-4
rotenone

: ((2R,6aR,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-ylidene)hydrazine

Conditions

Conditions	Yield
With sodium acetate; hydrazine hydrate In ethanol at 80℃; for 5h;	91%

: 1361382-43-5
6-(trimethylsilyl)hex-5-yn-1-yl 2-cyano-2-diazoacetate

: 83-79-4
rotenone

: C35H39NO8Si

Conditions

Conditions	Yield
With Rh2(esp)2 In dichloromethane at 22℃; for 4h; Inert atmosphere; diastereoselective reaction;	88%

: 83-79-4
rotenone

: (R)-5-(7,8-Dimethoxy-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl)-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

Conditions

Conditions	Yield
With potassium hydroxide; hydrazine In ethanol Heating;	87%
With hydrazine hydrate In ethanol

: 83-79-4
rotenone

: 58277-58-0
(6aS,12aS,5’R)-rotenone hydrobromide

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid at 20℃; for 0.5h;	87%

: 463-49-0
1,2-propanediene

: 83-79-4
rotenone

: C26H28O6

Conditions

Conditions	Yield
Stage #1: rotenone With copper diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In tetrahydrofuran for 0.0833333h; Inert atmosphere; Stage #2: 1,2-propanediene With (dimethoxy)methylsilane In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; diastereoselective reaction;	86%

: 100-63-0
phenylhydrazine

: 83-79-4
rotenone

: (R)-5-(7,8-Dimethoxy-3-phenyl-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl)-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

Conditions

Conditions	Yield
With potassium hydroxide In ethanol Heating;	85%

: 83-79-4
rotenone

: 30462-22-7
2-((2R,6aS,12aS)-8,9-dimethoxy-1,2,6,6a,12,12a-hexahydrochromeno[3,4-b]furo[2,3-h]chromen-2-yl)propan-2-ol

Conditions

Conditions	Yield
With iron(III)-acetylacetonate; methyl 4-nitrobenzenesulfonate; phenylsilane; sodium hydrogencarbonate In methanol at 0 - 20℃; for 12h; Schlenk technique; Inert atmosphere; regioselective reaction;	85%
Stage #1: rotenone With mercury(II) diacetate In tetrahydrofuran; water at 20℃; for 18h; Stage #2: With sodium tetrahydroborate; sodium hydrogencarbonate In tetrahydrofuran; water	48%
With sodium tetrahydroborate; mercury(II) diacetate 1) H2O, THF, 20 deg C, 10 h, 2) 30 s; Yield given. Multistep reaction;
Multi-step reaction with 3 steps 1: 1) H2, pyridine / 1) 5percent Pd-BaSO4 2: 0.37 g / m-chloroperbenzoic acid, NaHCO3 / CH2Cl2; H2O / 0.75 h / 19 °C 3: 66 percent / activated Zn-dust / methanol / Ambient temperature View Scheme

: 83-79-4
rotenone

: 811451-63-5
6aS,12aS-8,9-dimethoxy-2-(2-methyloxiran-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 2h;	85%

: 60-34-4
methylhydrazine

: 83-79-4
rotenone

: (R)-5-(7,8-Dimethoxy-3-methyl-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl)-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

Conditions

Conditions	Yield
With potassium hydroxide In ethanol Heating;	84%

: 83-79-4
rotenone

: 15130-81-1
(6aS,12aS,5′R)-rotenone-6′-norketone

Conditions

Conditions	Yield
With sodium periodate; osmium(VIII) oxide In tetrahydrofuran; water; tert-butyl alcohol	82%
With sodium periodate; osmium(VIII) oxide	46%

: 83-79-4
rotenone

: 509-96-6
12a-hydroxyrotenone

Conditions

Conditions	Yield
With potassium dichromate; acetic acid In water at 20 - 60℃; for 18.5h;	82%
With dichromate anion; acetic acid	51%

: 83-79-4
rotenone

: 82481-44-5
(2R,6S,6aS,12aS,2'R,6'S,6'aS,12'aS)-2,2'-Diisopropenyl-8,9,8',9'-tetramethoxy-1,2,12,12a,1',2',12',12'a-octahydro-6aH,6'aH-[6,6']bi[chromeno[3,4-b]furo[2,3-h]chromenyl]-6,6'-diol

Conditions

Conditions	Yield
In acetic acid; acetonitrile electrochemical reduction;	80%
In acetic acid; acetonitrile Product distribution; Mechanism; electrochemical reduction; variation of solvent;	80 % Chromat.

: 83-79-4
rotenone

: (6aS,12S,12aR,5′R)-6′,7′-dihydro-12-deoxo-12-hydroxyamorphigenin

Conditions

Conditions	Yield
Stage #1: rotenone With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 1.5h; Inert atmosphere; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 18h;	80%
Stage #1: rotenone With borane In tetrahydrofuran Reduction; hydroboration; Stage #2: With sodium hydroxide; dihydrogen peroxide Oxidation;

: 83-79-4
rotenone

: 3276-12-8
rotenol

Conditions

Conditions	Yield
In water; acetonitrile electrochemical reduction;	75%
With sodium hydroxide In ethanol Mechanism; Electrochemical reduction; tetrabutylammonium perchlorate, aqueous or aprotic medium;	70%
With sodium hydroxide In ethanol controlled potential electrolysis, tetrabutylammonium perchlorate; other solvent DMF;	70%

: 75-04-7
ethylamine

: 83-79-4
rotenone

: <1-(4-hydroxy-2-methylethenyl-2,3-dihydrobenzofuran-5-yl)-1-(6,7-dimethoxy-2H-chromen-4-yl)methylidene>ethylamine

Conditions

Conditions	Yield
In ethanol Product distribution; Heating; other amines, also with nitrenonone;	73%
In ethanol Heating;	73%

: 109-84-2
2-hydroxyethylhydrazine

: 83-79-4
rotenone

: (R)-5-[3-(2-Hydroxy-ethyl)-7,8-dimethoxy-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl]-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

Conditions

Conditions	Yield
With potassium hydroxide In ethanol Heating;	71%

: 70775-39-2, 5367-24-8
dimethylsulfoxonium methylide

: 83-79-4
rotenone

: 6a,12a-methanorotenol

Conditions

Conditions	Yield
In tetrahydrofuran 1.) room temperature, 10 min, 2.) 45-55 deg C, 50 min;	71%

: 58310-28-4
(Difluoromethyl)triphenylphosphonium bromide

: 83-79-4
rotenone

: (2R,6aS,12aS)-2-(2-bromo-4,4-difluorobutan-2-yl)-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one

Conditions

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III); copper(ll) bromide In N,N-dimethyl-formamide at 20℃; for 10h; Schlenk technique; Inert atmosphere; Irradiation;	71%

: 539-44-6
N-4-methylphenylhydrazine

: 83-79-4
rotenone

: (R)-5-(7,8-Dimethoxy-3-p-tolyl-3,3a,4,9b-tetrahydro-chromeno[3,4-c]pyrazol-1-yl)-2-isopropenyl-2,3-dihydro-benzofuran-4-ol

Conditions

Conditions	Yield
With potassium hydroxide In ethanol Heating;	70%

: 74-88-4
methyl iodide

: 83-79-4
rotenone

: 59456-14-3, 143838-84-0, 143838-90-8, 149116-35-8
(6aS,12aR,5'R)-/(6aR,12aS,5'R)-12a-methylrotenone

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;	66%

: 83-79-4
rotenone

: 1-(4-hydroxy-2-methylethenyl-2,3-dihydrobenzofuran-5-yl)-7,8-dimethoxy-1,9b,3a,4-tetrahydro-2H-<1>-benzopyrano<4,3-d>isoxazol-1-ene

Conditions

Conditions	Yield
With potassium hydroxide; hydroxylamine hydrochloride In ethanol for 3.5h; Heating;	66%

: 75-61-6
dibromodifluoromethane

: 83-79-4
rotenone

: (2R,6aS,12aS)-2-((R)-4-bromo-4,4-difluorobutan-2-yl)-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]-chromen-6(6aH)-one

Conditions

Conditions	Yield
Stage #1: dibromodifluoromethane; rotenone With tetrahydrofuran; eosin at 20℃; for 5h; Irradiation; Inert atmosphere; Schlenk technique; Stage #2: With potassium hydrogencarbonate for 5h; Inert atmosphere; Irradiation; Cooling with ice; Schlenk technique;	65%

: 75-61-6
dibromodifluoromethane

: 83-79-4
rotenone

: C24H23BrF2O6

Conditions

Conditions	Yield
With eosin y In tetrahydrofuran at 20℃; for 10h; Inert atmosphere;	65%

Rotenone History

Emmanuel Geoffroy first isolated rotenone from a specimen of Rotenone (CAS NO.83-79-4), now called Lonchocarpus nicou, while traveling in French Guiana.He wrote about this research in his thesis, published posthumously in 1895 after his death from a parasitic disease.Researchers later determined that the substance which Geoffroy termed nicouline was identically rotenone.

Rotenone Standards and Recommendations

OSHA PEL: TWA 5 mg/m³
ACGIH TLV: TWA 5 mg/m³; Not Classifiable as a Human Carcinogen
DFG MAK: 5 mg/m³

Rotenone Analytical Methods

For occupational chemical analysis use NIOSH: Rotenone, 5007.

Rotenone Specification

The systematic name of Rotenone is (2R,6aS,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one. With the CAS registry number 83-79-4, it is also named as (-)-cis-Rotenone. The product's categories are Miscellaneous Natural Products; Alpha sort; Botanicals Pesticides & Metabolites; Q-ZAnalytical Standards; Botanicals Analytical Standards; Alphabetic; Insecticides; Pesticides; R; Mitochondrial Inhibitors; Cell Stress; Nitric Oxide and Cell Stress; Asymmetric Synthesis; Chiral Building Blocks; Complex Molecules, and the other registry number is 12679-58-2. Besides, it is white or off-white powder, which should be sealed in plastic bags in a cool, dry and ventilated place. It is stable, but light and air sensitive. In addition, its molecular formula is C₂₃H₂₂O₆ and molecular weight is 394.42.

The other characteristics of Rotenonecan be summarized as:
(1)EINECS: 201-501-9; (2)ACD/LogP: 4.65; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 4.65; (5)ACD/LogD (pH 7.4): 4.65; (6)ACD/BCF (pH 5.5): 2007.36; (7)ACD/BCF (pH 7.4): 2007.36; (8)ACD/KOC (pH 5.5): 8046.68; (9)ACD/KOC (pH 7.4): 8046.68; (10)#H bond acceptors: 6; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 3; (13)Index of Refraction: 1.591; (14)Molar Refractivity: 104.92 cm³; (15)Molar Volume: 310.2 cm³; (16)Surface Tension: 45.3 dyne/cm; (17)Density: 1.271 g/cm³; (18)Flash Point: 244.6 °C; (19)Melting Point: 159-164 °C; (20)alpha: -115 °(c=1.4 in chloroform); (21)Water Solubility: 0.2 mg/L at 20 °C; (22)Enthalpy of Vaporization: 84.22 kJ/mol; (23)Boiling Point: 559.8 °C at 760 mmHg; (24)Vapour Pressure: 1.45E-12 mmHg at 25 °C.

Preparation of Rotenone:
This chemical can be prepared by extraction from the roots and stems of several tropical and subtropical plant species with organic solvents. And then concentrate extract liquor. At last, you would obtain this chemical after filtration and crystallization.

Uses of Rotenone:
Rotenone:can be used as a broad-spectrum insecticide, piscicide, and pesticide. It is also used for studying of the biodiversity of marine fishes to collect cryptic, or hidden, fishes by fish researchers. And it has been used to reduce parasitic mites on chickens and other fowl in powdered form. Furthermore, it is used for the garden as an excellent organic pesticide dust.

Safety Information of Rotenone:
When you are using Rotenone, please be cautious about it as the following: it is toxic if swallowed. Please do not breathe dust. It is also irritating to eyes, respiratory system and skin. Youi should wear suitable protective clothing to avoid contact with skin and eyes. Moreover, this chemical is very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. And this material and its container must be disposed of as hazardous waste. Please avoid release to the environment, and refer to special instructions / safety data sheets. Additionally, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C2c5ccc1O[C@@H](C(=C)\C)Cc1c5O[C@H]3[C@@H]2c4c(OC3)cc(OC)c(OC)c4
(2)InChI: InChI=1/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1
(3)InChIKey: JUVIOZPCNVVQFO-HBGVWJBIBF

The toxicity data of Rotenone is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LDLo	intravenous	650ug/kg (0.65mg/kg)	BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION GASTROINTESTINAL: NAUSEA OR VOMITING	Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
dog	LDLo	intravenous	650ug/kg (0.65mg/kg)	BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION GASTROINTESTINAL: NAUSEA OR VOMITING	Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
dog	LDLo	oral	300mg/kg (300mg/kg)	GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH GASTROINTESTINAL: NAUSEA OR VOMITING	Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
duck	LD50	oral	> 2gm/kg (2000mg/kg)		Down to Earth. Vol. 35, Pg. 25, 1979.
frog	LDLo	oral	4mg/kg (4mg/kg)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
guinea pig	LDLo	intraperitoneal	10mg/kg (10mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Proceedings of the Society for Experimental Biology and Medicine. Vol. 34, Pg. 135, 1936.
guinea pig	LDLo	oral	100mg/kg (100mg/kg)	LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH	Proceedings of the Society for Experimental Biology and Medicine. Vol. 34, Pg. 135, 1936.
human	LDLo	oral	143mg/kg (143mg/kg)	GASTROINTESTINAL: OTHER CHANGES	"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 521, 1969.
man	LDLo	unreported	294mg/kg (294mg/kg)		"Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse	LD50	intraperitoneal	2650ug/kg (2.65mg/kg)		Radiation Research. Vol. 91, Pg. 186, 1982.
mouse	LD50	oral	2800ug/kg (2.8mg/kg)		EHP, Environmental Health Perspectives. Vol. 14, Pg. 109, 1976.
pig	LDLo	oral	3700ug/kg (3.7mg/kg)	BEHAVIORAL: ATAXIA GASTROINTESTINAL: NAUSEA OR VOMITING LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Journal of the American Veterinary Medical Association. Vol. 130, Pg. 410, 1957.
pigeon	LDLo	intravenous	1mg/kg (1mg/kg)	BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION GASTROINTESTINAL: NAUSEA OR VOMITING	Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rabbit	LD50	skin	> 1gm/kg (1000mg/kg)		Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 5, 1978.
rabbit	LDLo	intramuscular	5mg/kg (5mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rabbit	LDLo	intravenous	350ug/kg (0.35mg/kg)	BEHAVIORAL: ATAXIA BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION	Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rabbit	LDLo	oral	1600mg/kg (1600mg/kg)	GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rabbit	LDLo	subcutaneous	20mg/kg (20mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rat	LCLo	inhalation	500mg/m³/30M (500mg/m³)		Farmaco, Edizione Scientifica. Vol. 20, Pg. 270, 1965.
rat	LD50	intraperitoneal	1600ug/kg (1.6mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP BEHAVIORAL: COMA	Farmaco, Edizione Scientifica. Vol. 20, Pg. 270, 1965.
rat	LD50	intravenous	200ug/kg (0.2mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: COMA CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP	Farmaco, Edizione Scientifica. Vol. 20, Pg. 270, 1965.
rat	LD50	oral	60mg/kg (60mg/kg)		Down to Earth. Vol. 35, Pg. 25, 1979.
rat	LD50	skin	> 940mg/kg (940mg/kg)		World Review of Pest Control. Vol. 9, Pg. 119, 1970.
rat	LD50	unreported	132mg/kg (132mg/kg)		Journal of Environmental Science and Health, Part B: Pesticides, Food Contaminants, and Agricultural Wastes. Vol. 15, Pg. 929, 1980.

Product Name

ROTENONE

Synthetic route

Rotenone History

Rotenone Standards and Recommendations

Rotenone Analytical Methods

Rotenone Specification

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