Forskolin supplier | CasNO.66575-29-9

Name
FORSKOLIN
EINECS 266-410-9
CAS No. 66575-29-9
Article Data9
CAS DataBase
Density 1.23 g/cm³
Solubility Soluble in ethanol, dimethylsulfoxide and chloroform. Insolule in water.
Melting Point 282-232 °C
Formula C₂₂H₃₄O₇
Boiling Point 519.9 °C at 760 mmHg
Molecular Weight 410.508
Flash Point 171.8 °C
Transport Information
Appearance Colorless crystalline solid
Safety 22-36/37
Risk Codes 21
Molecular Structure
Hazard Symbols Xn
Synonyms 1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-,[3R-(3a,4ab,5b,6b,6aa,10a,10ab,10ba)]-;(-)-Forskolin;Coleonol;ForsLean;HL 362;NSC 357088;NSC 375489;
PSA 113.29000
LogP 1.51990

Synthetic route

: 108-24-7
acetic anhydride

: 64657-20-1
7-deacetyl forskolin

: 66575-29-9
forskolin

Conditions

Conditions	Yield
In pyridine at 0℃; for 18h;	100%
With pyridine at 0 - 20℃; for 18h;	100%
With pyridine at 0℃; for 20h;	83%

: 220423-84-7
(13R)-Spiroforskolin

: 66575-29-9
forskolin

Conditions

Conditions	Yield
In methanol for 96h;

: 64657-20-1
7-deacetyl forskolin

: 75-36-5
acetyl chloride

A: 64657-21-2
(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-6-(acetyloxy)-3-ethenyldodecahydro-5,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1H-naphtho[2,1-b]pyran-1-one

B: 66575-29-9
forskolin

C: 1-acetyl-7-deacetylforskolin

Conditions

Conditions	Yield
With diisopropylamine In toluene for 3h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 3h; Ambient temperature; Yield given. Yields of byproduct given;

...Expand

: 898546-13-9
(1S,6S,12S,16S,2R)-14-hydroxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.0.2,607,12]heptadecan-11-one

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C 2: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 3: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 4: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 5: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 6: 100 percent / pyridine / 18 h / 0 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
2: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
3: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
4: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
5: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
6: 100 percent / pyridine / 18 h / 0 °C
View Scheme

: 93108-68-0
(2S,7S,13S,14S,6R,9R)-14-hydroxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.02,607,12]heptadec-11-one

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 2: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 3: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 4: 100 percent / pyridine / 18 h / 0 °C View Scheme

: 898546-12-8
(1S,6S,12S,16S,2R,11R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.0.2,607,12]heptadec-14-en-11-ol

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C 2: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C 3: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 4: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 5: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 6: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 7: 100 percent / pyridine / 18 h / 0 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
2: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
3: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
4: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
5: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
6: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
7: 100 percent / pyridine / 18 h / 0 °C
View Scheme

: 115155-11-8
(1S,6S,11S,12S,2R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.0.2,607,12]heptadec-14-en-11-ol

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 2: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 3: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 4: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 5: 100 percent / pyridine / 18 h / 0 °C View Scheme

: 115155-09-4
(1S,6S,11S,12S,2R,16R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.02,607,12]heptadec-13-en-11-ol

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 2: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 3: 100 percent / pyridine / 18 h / 0 °C View Scheme

: 898546-14-0
(6S,11S,16S,1R,2R,12R,13R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.0.2,607,12]heptadec-14-en-11,13-diol

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 2: 100 percent / pyridine / 18 h / 0 °C View Scheme

: 157201-96-2
(1S,7S,9S,3R,5R,8R,14R)-14-acetyloxy-8,9-dihydroxy-1,5,7,11,11-pentamethyl-6-oxa-5-vinyltricyclo[8.4.0.02,7]tetradec-3-yl acetate

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 93 percent / p-toluenesulfonic acid / 24 h / 50 °C 2: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C 3: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C 4: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C 5: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C 6: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C 7: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 8: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 9: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 10: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 11: 100 percent / pyridine / 18 h / 0 °C View Scheme

Yield

Multi-step reaction with 11 steps
1: 93 percent / p-toluenesulfonic acid / 24 h / 50 °C
2: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C
3: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C
4: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C
5: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
6: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
7: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
8: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
9: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
10: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
11: 100 percent / pyridine / 18 h / 0 °C
View Scheme

: ptychantin A

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: 100 percent / potassium hydroxide / methanol / 13.5 h / 20 °C 2: 93 percent / p-toluenesulfonic acid / 24 h / 50 °C 3: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C 4: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C 5: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C 6: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C 7: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C 8: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 9: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 10: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 11: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 12: 100 percent / pyridine / 18 h / 0 °C View Scheme

Yield

Multi-step reaction with 12 steps
1: 100 percent / potassium hydroxide / methanol / 13.5 h / 20 °C
2: 93 percent / p-toluenesulfonic acid / 24 h / 50 °C
3: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C
4: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C
5: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C
6: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
7: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
8: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
9: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
10: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
11: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
12: 100 percent / pyridine / 18 h / 0 °C
View Scheme

: ptychantin B

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: 89 percent / potassium hydroxide / methanol / 13.5 h / 20 °C 2: 93 percent / p-toluenesulfonic acid / 24 h / 50 °C 3: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C 4: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C 5: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C 6: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C 7: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C 8: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 9: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 10: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 11: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 12: 100 percent / pyridine / 18 h / 0 °C View Scheme

Yield

Multi-step reaction with 12 steps
1: 89 percent / potassium hydroxide / methanol / 13.5 h / 20 °C
2: 93 percent / p-toluenesulfonic acid / 24 h / 50 °C
3: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C
4: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C
5: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C
6: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
7: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
8: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
9: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
10: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
11: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
12: 100 percent / pyridine / 18 h / 0 °C
View Scheme

: 537038-62-3
(2S,7S,13S,6R,9R,14R)-14-hydroxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.02,6.07,12]heptadecan-11-one

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C 2: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C 3: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C 4: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 5: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 6: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 7: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 8: 100 percent / pyridine / 18 h / 0 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C
2: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
3: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
4: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
5: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
6: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
7: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
8: 100 percent / pyridine / 18 h / 0 °C
View Scheme

: 536742-35-5
(1S,6S,12S,2R,11R,14R,16R)-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.02,6.07,12]heptadecane-11,14-diol

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C 2: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C 3: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C 4: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C 5: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 6: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 7: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 8: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 9: 100 percent / pyridine / 18 h / 0 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C
2: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C
3: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
4: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
5: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
6: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
7: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
8: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
9: 100 percent / pyridine / 18 h / 0 °C
View Scheme

: 536742-34-4
(2S,7S,13S,6R,9R,11R,14R)-14-acetyloxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.02,6.07,12]heptadec-11-yl acetate

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C 2: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C 3: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C 4: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C 5: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C 6: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 7: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C 8: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C 9: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C 10: 100 percent / pyridine / 18 h / 0 °C View Scheme

Yield

Multi-step reaction with 10 steps
1: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C
2: 89 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C
3: 54 percent / potassium hydride / tetrahydrofuran / 0.5 h / 0 °C
4: 80 percent / pyridine; chromium oxide / CH2Cl2 / 24 h / 20 °C
5: 100 percent / sodium / 2-methyl-propan-2-ol / 29 h / 30 °C
6: 100 percent / aqueous hydrochloric acid / tetrahydrofuran / 1 h / 20 °C
7: 96 percent / potassium hydride / tetrahydrofuran / 0.13 h / 20 °C
8: 61 percent / potassium carbonate; m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / 0 °C
9: 59 percent / perchloric acid / tetrahydrofuran / 264 h / 20 °C
10: 100 percent / pyridine / 18 h / 0 °C
View Scheme

: 123218-03-1, 123218-04-2
rac-5α<<(tert-Butyl)dimethylsilyl>oxy>-4β-ethinyl-1,4,4a,5,6,7,8,8aα-octahydro-4-hydroxy-3,4aα,8,8-tetramethylnaphthalin-1(4H)-on

A: C22H34O7

B: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C 2.1: dmap / N,N-dimethyl-formamide / 13 h / 65 °C 3.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve 4.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C 5.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C 6.1: triethylamine / chloroform / 1 h / 23 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 8.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 9.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 10.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 11.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 12.1: n-butyllithium / hexane / 0.5 h / 23 °C 12.2: 1.17 h / -78 - -30 °C 13.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 14.1: pyridine / 20 h / 0 °C 15.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate View Scheme

Yield

Multi-step reaction with 15 steps
1.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C
2.1: dmap / N,N-dimethyl-formamide / 13 h / 65 °C
3.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve
4.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
5.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
6.1: triethylamine / chloroform / 1 h / 23 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
8.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
9.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
10.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
11.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
12.1: n-butyllithium / hexane / 0.5 h / 23 °C
12.2: 1.17 h / -78 - -30 °C
13.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
14.1: pyridine / 20 h / 0 °C
15.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme

: 123218-03-1, 123218-04-2
rac-5α<<(tert-Butyl)dimethylsilyl>oxy>-4β-ethinyl-1,4,4a,5,6,7,8,8aα-octahydro-4-hydroxy-3,4aα,8,8-tetramethylnaphthalin-1(4H)-on

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 17 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C 2.1: dmap / N,N-dimethyl-formamide / 13 h / 65 °C 3.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve 4.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C 5.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C 6.1: triethylamine / chloroform / 1 h / 23 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 8.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 9.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 10.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 11.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 12.1: n-butyllithium / hexane / 0.5 h / 23 °C 12.2: 1.17 h / -78 - -30 °C 13.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 14.1: pyridine / 20 h / 0 °C 15.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C 16.1: potassium carbonate / methanol; water / 6 h / 23 °C 17.1: pyridine / 20 h / 0 °C View Scheme

Yield

Multi-step reaction with 17 steps
1.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C
2.1: dmap / N,N-dimethyl-formamide / 13 h / 65 °C
3.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve
4.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
5.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
6.1: triethylamine / chloroform / 1 h / 23 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
8.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
9.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
10.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
11.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
12.1: n-butyllithium / hexane / 0.5 h / 23 °C
12.2: 1.17 h / -78 - -30 °C
13.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
14.1: pyridine / 20 h / 0 °C
15.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
16.1: potassium carbonate / methanol; water / 6 h / 23 °C
17.1: pyridine / 20 h / 0 °C
View Scheme

: C22H38O3Si

A: C22H34O7

B: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1.1: dmap / N,N-dimethyl-formamide / 13 h / 65 °C 2.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve 3.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C 4.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C 5.1: triethylamine / chloroform / 1 h / 23 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 7.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 8.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 9.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 10.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 11.1: n-butyllithium / hexane / 0.5 h / 23 °C 11.2: 1.17 h / -78 - -30 °C 12.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 13.1: pyridine / 20 h / 0 °C 14.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate View Scheme

Yield

Multi-step reaction with 14 steps
1.1: dmap / N,N-dimethyl-formamide / 13 h / 65 °C
2.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve
3.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
4.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
5.1: triethylamine / chloroform / 1 h / 23 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
7.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
8.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
9.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
10.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
11.1: n-butyllithium / hexane / 0.5 h / 23 °C
11.2: 1.17 h / -78 - -30 °C
12.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
13.1: pyridine / 20 h / 0 °C
14.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme

: C22H38O3Si

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 16 steps 1.1: dmap / N,N-dimethyl-formamide / 13 h / 65 °C 2.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve 3.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C 4.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C 5.1: triethylamine / chloroform / 1 h / 23 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 7.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 8.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 9.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 10.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 11.1: n-butyllithium / hexane / 0.5 h / 23 °C 11.2: 1.17 h / -78 - -30 °C 12.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 13.1: pyridine / 20 h / 0 °C 14.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C 15.1: potassium carbonate / methanol; water / 6 h / 23 °C 16.1: pyridine / 20 h / 0 °C View Scheme

Yield

Multi-step reaction with 16 steps
1.1: dmap / N,N-dimethyl-formamide / 13 h / 65 °C
2.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve
3.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
4.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
5.1: triethylamine / chloroform / 1 h / 23 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
7.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
8.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
9.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
10.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
11.1: n-butyllithium / hexane / 0.5 h / 23 °C
11.2: 1.17 h / -78 - -30 °C
12.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
13.1: pyridine / 20 h / 0 °C
14.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
15.1: potassium carbonate / methanol; water / 6 h / 23 °C
16.1: pyridine / 20 h / 0 °C
View Scheme

: C29H42O4Si

A: C22H34O7

B: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve 2.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C 3.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C 4.1: triethylamine / chloroform / 1 h / 23 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 6.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 7.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 8.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 9.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 10.1: n-butyllithium / hexane / 0.5 h / 23 °C 10.2: 1.17 h / -78 - -30 °C 11.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 12.1: pyridine / 20 h / 0 °C 13.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate View Scheme

Yield

Multi-step reaction with 13 steps
1.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve
2.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
3.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
4.1: triethylamine / chloroform / 1 h / 23 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
6.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
7.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
8.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
9.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
10.1: n-butyllithium / hexane / 0.5 h / 23 °C
10.2: 1.17 h / -78 - -30 °C
11.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
12.1: pyridine / 20 h / 0 °C
13.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme

: C29H42O4Si

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve 2.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C 3.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C 4.1: triethylamine / chloroform / 1 h / 23 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 6.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 7.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 8.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 9.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 10.1: n-butyllithium / hexane / 0.5 h / 23 °C 10.2: 1.17 h / -78 - -30 °C 11.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 12.1: pyridine / 20 h / 0 °C 13.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C 14.1: potassium carbonate / methanol; water / 6 h / 23 °C 15.1: pyridine / 20 h / 0 °C View Scheme

Yield

Multi-step reaction with 15 steps
1.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 72 h / 30 °C / Molecular sieve
2.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
3.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
4.1: triethylamine / chloroform / 1 h / 23 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
6.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
7.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
8.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
9.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
10.1: n-butyllithium / hexane / 0.5 h / 23 °C
10.2: 1.17 h / -78 - -30 °C
11.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
12.1: pyridine / 20 h / 0 °C
13.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
14.1: potassium carbonate / methanol; water / 6 h / 23 °C
15.1: pyridine / 20 h / 0 °C
View Scheme

: C29H40O4Si

A: C22H34O7

B: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C 2.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C 3.1: triethylamine / chloroform / 1 h / 23 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 5.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 6.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 7.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 8.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 9.1: n-butyllithium / hexane / 0.5 h / 23 °C 9.2: 1.17 h / -78 - -30 °C 10.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 11.1: pyridine / 20 h / 0 °C 12.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate View Scheme

Yield

Multi-step reaction with 12 steps
1.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
2.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
3.1: triethylamine / chloroform / 1 h / 23 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
5.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
6.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
7.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
8.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
9.1: n-butyllithium / hexane / 0.5 h / 23 °C
9.2: 1.17 h / -78 - -30 °C
10.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
11.1: pyridine / 20 h / 0 °C
12.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme

: C29H40O4Si

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C 2.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C 3.1: triethylamine / chloroform / 1 h / 23 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 5.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 6.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 7.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 8.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 9.1: n-butyllithium / hexane / 0.5 h / 23 °C 9.2: 1.17 h / -78 - -30 °C 10.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 11.1: pyridine / 20 h / 0 °C 12.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C 13.1: potassium carbonate / methanol; water / 6 h / 23 °C 14.1: pyridine / 20 h / 0 °C View Scheme

Yield

Multi-step reaction with 14 steps
1.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
2.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
3.1: triethylamine / chloroform / 1 h / 23 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
5.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
6.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
7.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
8.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
9.1: n-butyllithium / hexane / 0.5 h / 23 °C
9.2: 1.17 h / -78 - -30 °C
10.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
11.1: pyridine / 20 h / 0 °C
12.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
13.1: potassium carbonate / methanol; water / 6 h / 23 °C
14.1: pyridine / 20 h / 0 °C
View Scheme

: C22H38O3Si

A: C22H34O7

B: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C 2.1: triethylamine / chloroform / 1 h / 23 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 4.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 5.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 6.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 7.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 8.1: n-butyllithium / hexane / 0.5 h / 23 °C 8.2: 1.17 h / -78 - -30 °C 9.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 10.1: pyridine / 20 h / 0 °C 11.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate View Scheme

Yield

Multi-step reaction with 11 steps
1.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
2.1: triethylamine / chloroform / 1 h / 23 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
4.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
5.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
6.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
7.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
8.1: n-butyllithium / hexane / 0.5 h / 23 °C
8.2: 1.17 h / -78 - -30 °C
9.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
10.1: pyridine / 20 h / 0 °C
11.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme

: C22H38O3Si

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C 2.1: triethylamine / chloroform / 1 h / 23 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 4.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 5.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 6.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 7.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 8.1: n-butyllithium / hexane / 0.5 h / 23 °C 8.2: 1.17 h / -78 - -30 °C 9.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 10.1: pyridine / 20 h / 0 °C 11.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C 12.1: potassium carbonate / methanol; water / 6 h / 23 °C 13.1: pyridine / 20 h / 0 °C View Scheme

Yield

Multi-step reaction with 13 steps
1.1: pyridinium p-toluenesulfonate / dichloromethane / 0.25 h / 23 °C
2.1: triethylamine / chloroform / 1 h / 23 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
4.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
5.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
6.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
7.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
8.1: n-butyllithium / hexane / 0.5 h / 23 °C
8.2: 1.17 h / -78 - -30 °C
9.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
10.1: pyridine / 20 h / 0 °C
11.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
12.1: potassium carbonate / methanol; water / 6 h / 23 °C
13.1: pyridine / 20 h / 0 °C
View Scheme

: C25H42O3Si

A: C22H34O7

B: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: triethylamine / chloroform / 1 h / 23 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 3.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 4.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 5.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 6.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 7.1: n-butyllithium / hexane / 0.5 h / 23 °C 7.2: 1.17 h / -78 - -30 °C 8.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 9.1: pyridine / 20 h / 0 °C 10.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate View Scheme

Yield

Multi-step reaction with 10 steps
1.1: triethylamine / chloroform / 1 h / 23 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
3.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
4.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
5.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
6.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
7.1: n-butyllithium / hexane / 0.5 h / 23 °C
7.2: 1.17 h / -78 - -30 °C
8.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
9.1: pyridine / 20 h / 0 °C
10.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme

: C25H42O3Si

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: triethylamine / chloroform / 1 h / 23 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 3.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 4.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 5.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 6.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 7.1: n-butyllithium / hexane / 0.5 h / 23 °C 7.2: 1.17 h / -78 - -30 °C 8.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 9.1: pyridine / 20 h / 0 °C 10.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C 11.1: potassium carbonate / methanol; water / 6 h / 23 °C 12.1: pyridine / 20 h / 0 °C View Scheme

Yield

Multi-step reaction with 12 steps
1.1: triethylamine / chloroform / 1 h / 23 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
3.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
4.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
5.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
6.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
7.1: n-butyllithium / hexane / 0.5 h / 23 °C
7.2: 1.17 h / -78 - -30 °C
8.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
9.1: pyridine / 20 h / 0 °C
10.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
11.1: potassium carbonate / methanol; water / 6 h / 23 °C
12.1: pyridine / 20 h / 0 °C
View Scheme

: C27H45NO4Si

A: C22H34O7

B: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 2.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 3.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 4.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 5.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 6.1: n-butyllithium / hexane / 0.5 h / 23 °C 6.2: 1.17 h / -78 - -30 °C 7.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 8.1: pyridine / 20 h / 0 °C 9.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate View Scheme

Yield

Multi-step reaction with 9 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
2.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
3.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
4.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
5.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
6.1: n-butyllithium / hexane / 0.5 h / 23 °C
6.2: 1.17 h / -78 - -30 °C
7.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
8.1: pyridine / 20 h / 0 °C
9.1: Chiralpak® AD-H / hexane; ethanol / Resolution of racemate
View Scheme

: C27H45NO4Si

: 66575-29-9
forskolin

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve 2.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C 3.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C 4.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique 5.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C 6.1: n-butyllithium / hexane / 0.5 h / 23 °C 6.2: 1.17 h / -78 - -30 °C 7.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C 8.1: pyridine / 20 h / 0 °C 9.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C 10.1: potassium carbonate / methanol; water / 6 h / 23 °C 11.1: pyridine / 20 h / 0 °C View Scheme

Yield

Multi-step reaction with 11 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 23 °C / Molecular sieve
2.1: citric acid; potassium osmate; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 120 h / 23 °C
3.1: toluene-4-sulfonic acid / acetone / 48 h / 23 °C
4.1: hydrogen / ethanol / 6 h / 23 °C / Schlenk technique
5.1: hydrogenchloride / toluene; 1,4-dioxane / 3 h / 23 °C
6.1: n-butyllithium / hexane / 0.5 h / 23 °C
6.2: 1.17 h / -78 - -30 °C
7.1: toluene-4-sulfonic acid / water; tetrahydrofuran / 288 h / 23 °C
8.1: pyridine / 20 h / 0 °C
9.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
10.1: potassium carbonate / methanol; water / 6 h / 23 °C
11.1: pyridine / 20 h / 0 °C
View Scheme

: 66575-29-9
forskolin

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: C23H32O7S

Conditions

Conditions	Yield
With dmap In dichloromethane at 20℃; for 4h; Inert atmosphere;	97%

: 75-77-4
chloro-trimethyl-silane

: 66575-29-9
forskolin

: 84010-19-5
1-(trimethylsilyl)forskolin

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 22℃; for 2h; Inert atmosphere;	92%
With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane at 80 - 85℃; for 2h;	77%

: 88920-24-5
p-methoxybenzyloxy acetic acid

: 66575-29-9
forskolin

: 120370-89-0
7β-acetoxy-6β,9α-dihydroxy-8,13-epoxy-1α-<(4-methoxybenzyloxy)acetoxy>labd-14-en-11-one

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate for 3h; Ambient temperature;	92%

: 66575-29-9
forskolin

: 77-76-9
2,2-dimethoxy-propane

: 119603-26-8
C25H38O7

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 0 - 20℃; for 6h; Inert atmosphere;	92%

: 97-94-9
triethyl borane

: 66575-29-9
forskolin

: 623-48-3
ethyl iodoacetae

: C28H45BO9

Conditions

Conditions	Yield
With 4-tert-Butylcatechol; sodium hydrogencarbonate In dichloromethane; benzene at 20℃; for 3h; Darkness;	91%

...Expand

: 66575-29-9
forskolin

: 64657-24-5
14,15-dihydroforskolin

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃;	90%
palladium-carbon In methanol

: 66575-29-9
forskolin

: 81873-10-1
1-deoxy-1-oxoforskolin

Conditions

Conditions	Yield
With 4-methyl-morpholine; 6C13H13P4CF3O3S(1-)2Ru(2+); acetone at 65℃; for 3h; Inert atmosphere; Sealed tube;	88%
With Collins oxidation agent In dichloromethane for 2.5h;	1.2 g

: 66575-29-9
forskolin

: 107-18-6
allyl alcohol

: 1,9-O-[(3-allyloxy)propylidene]forskolin

Conditions

Conditions	Yield
With ammonium cerium (IV) nitrate In acetonitrile at 20℃; for 24h; Inert atmosphere; regioselective reaction;	87%

: 75-44-5
phosgene

: 66575-29-9
forskolin

: 81826-81-5
forskolin 1,9-carbonate

Conditions

Conditions	Yield
With pyridine In toluene at 0 - 20℃; for 4.5h;	86%
With pyridine In toluene at 0℃; for 1h;	1.22 g

: 4-[(dimethylamino)methyl]benzoic acid hydrochloride

: 66575-29-9
forskolin

: 7β-acetoxy-6β,9α-dihydroxy-1α-(4-dimethylaminomethylbenzoyloxy)-8,13-epoxy-labd-14-en-11-one hydrochloride

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 16h;	82.3%

: 66575-29-9
forskolin

: 64657-20-1
7-deacetyl forskolin

Conditions

Conditions	Yield
With ethylenediamine In methanol for 0.0833333h; Microwave irradiation;	80%
With sodium hydroxide In methanol; water
With potassium carbonate In methanol at 25℃; for 0.75h;
With water first-order plots of degradation in water and phosphate buffer (pH 6.0-8.0);
In methanol; potassium carbonate

: 66575-29-9
forskolin

: 18162-48-6
tert-butyldimethylsilyl chloride

: 105559-76-0
7β-acetoxy-1α-<(tert-butyldimethylsilyl)oxy>-6β,9α-dihydroxy-8,13-epoxylabd-14-en-11-one

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 70℃; for 22h;	80%

: 66575-29-9
forskolin

: 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde

: 1,9-O-(N-propargyl-3-indolylidene)forskolin

Conditions

Conditions	Yield
With Amberlist-15 wet In 1,2-dichloro-ethane at 20℃; for 24h;	75%

: 66575-29-9
forskolin

: 67-64-1
acetone

: 119603-26-8
C25H38O7

Conditions

Conditions	Yield
With aluminium trichloride In diethyl ether for 0.3h; Ambient temperature;	74%

: 66575-29-9
forskolin

: 98-88-4
benzoyl chloride

: 84048-17-9
1-benzoylforskolin

Conditions

Conditions	Yield
With pyridine Ambient temperature;	72%

: 66575-29-9
forskolin

: 75-36-5
acetyl chloride

: 84010-29-7
Acetic acid (3S,4aR,5S,6S,6aS,10S,10aR,10bS)-5-acetoxy-3-ethyl-6,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-benzo[f]chromen-10-yl ester

Conditions

Conditions	Yield
With pyridine Ambient temperature;	72%

: 97-94-9
triethyl borane

: 65492-21-9
((Iodomethyl)sulfonyl)benzene

: 66575-29-9
forskolin

: C31H45BO9S

Conditions

Conditions	Yield
With 4-tert-Butylcatechol; sodium hydrogencarbonate In dichloromethane; benzene at 20℃; for 3h; Darkness;	63%

...Expand

: 3282-30-2
pivaloyl chloride

: 66575-29-9
forskolin

: 84010-28-6
7-deacetyl-1,7-dipivaloylforskolin

Conditions

Conditions	Yield
With pyridine Ambient temperature;	55%

: 66575-29-9
forskolin

: 98-88-4
benzoyl chloride

: 84048-21-5
C34H40O8

Conditions

Conditions	Yield
With pyridine Ambient temperature;	55%

: 66575-29-9
forskolin

: 84010-25-3
forskolin-14,15-dibromide

Conditions

Conditions	Yield
With bromine In carbon disulfide at 0 - 20℃; for 2.75h;	50%

: 66575-29-9
forskolin

: 103-71-9
phenyl isocyanate

: 84048-18-0
1-(anilinocarbonyl)forskolin

Conditions

Conditions	Yield
In toluene for 20h; Heating;	48%

: 66575-29-9
forskolin

: 64657-21-2, 66428-90-8, 66701-90-4, 67921-06-6, 132620-09-8
coleonol-B

Conditions

Conditions	Yield
	47%

: 66575-29-9
forskolin

: 220423-84-7
(13R)-Spiroforskolin

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In benzene at 0 - 5℃;	45%

: 66575-29-9
forskolin

: 65-85-0
benzoic acid

: 132620-05-4
1β-Benzoyloxy-1-deoxycoleonol

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 36h; Ambient temperature;	45%

: 66575-29-9
forskolin

A: 144426-70-0, 144539-48-0
7β-acetoxy-8,13-epoxy-6β-hydroxy-11-oxolabd-14-ene-1α,9α-diyl cyclo-α-phosphite

B: 144426-70-0, 144539-48-0
7β-acetoxy-8,13-epoxy-6β-hydroxy-11-oxolabd-14-ene-1α,9α-diyl cyclo-β-phosphite

Conditions

Conditions	Yield
With pyridine; bis(trifluoroethyl)hydrogen phosphite for 16h; Ambient temperature;	A 39% B 13%

: 66575-29-9
forskolin

: 106-96-7
propargyl bromide

A: 1350721-63-9
1-O-propargyl-forskolin

B: 1350721-66-2
1-O-propargyl-6-O-acetyl-7-deacetyl-forskolin

Conditions

Conditions	Yield
With potassium carbonate; sodium iodide In acetone at 20℃; Reflux;	A 36% B 35%
With potassium carbonate; potassium iodide In acetone for 24h; Reflux;	A 1.8 g B 1.7 g

...Expand

: 66575-29-9
forskolin

A: 144426-66-4, 144491-36-1
7β-acetoxy-8,13-epoxy-6β-hydroxy-11-oxolabd-14-ene-1α,9α-diyl cyclophospho-α-chloridate

B: 144426-66-4, 144491-36-1
7β-acetoxy-8,13-epoxy-6β-hydroxy-11-oxolabd-14-ene-1α,9α-diyl cyclophospho-β-chloridate

Conditions

Conditions	Yield
With pyridine; triethylamine; trichlorophosphate In diethyl ether 1) -10 deg C, 1 h, 2) RT, 60 h; other substrate, various phosphorylating agents;	A 33% B 12%
With pyridine; triethylamine; trichlorophosphate In diethyl ether 1) -10 deg C, 1 h, 2) RT, 60 h;	A 33% B 12%

: 66575-29-9
forskolin

: 99-33-2
3,5-dinitrobenoyl chloride

: 6β-acetoxy-7β-(3,5-dinitro)benzoyloxy-8,13-epoxy-1α,9-dihydroxy-labd-14-en-11-one

Conditions

Conditions	Yield
With pyridine at 20℃; for 1.5h;	31%

: 66575-29-9
forskolin

: 144426-76-6
7β-acetoxy-8,13-epoxy-6β,9α-dihydroxy-11-oxolabd-14-en-1α-yl dihydrogen phosphate

Conditions

Conditions	Yield
With dihydro-(1,2-dibromo-2-phenyl-1-ethyl)phosphonic acid; N-ethyl-N,N-diisopropylamine In dichloromethane for 48h; Ambient temperature;	30%

Forskolin Chemical Properties

IUPAC Name: (3-Ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2H-benzo[f]chromen-5-yl) acetate
Systematic of 1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-,(3R,4aR,5S,6S,6aS,10S,10aR,10bS)- (CAS NO.66575-29-9 ): 3R,4aR,5S,6S,6aS,10S,10aR,10bS)-Dodecahydro-5,6,10,10b-tetrahydroxy-3,4a,7,7,10a-pentamethyl-3-vinyl-1H-naphtho(2,1-b)pyran-1-one 5-acetate ; 1H-Naphtho(2,1-b)pyran-1-one, 5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-, (3R-(3alpha,4abeta,5beta,6beta,6aalpha,10alpha,10abeta,10balpha))- ; 7-beta-Acetoxy-8,13-epoxy-1-alpha,6-beta,9-alpha-trihydroxylabd-14-en-11-one ; Boforsin ; Colforsinum [Latin] ; EINECS 266-410-9 ; Forskolin ; HL 362 ; L 75 1362B ; M 410 ; NSC 357088 ; NSC 375489 ; UNII-1F7A44V6OU
CAS NO: 66575-29-9
Classification Code: Adjuvants, Immunologic ; Anti-Asthmatic Agents ; Antiglaucoma agent ; Autonomic Agents ; Bronchodilator Agents ; Cardiotonic Agents ; Cardiovascular Agents ; Drug / Therapeutic Agent ; Immunologic Factors ; Natural Product ; Peripheral Nervous System Agents ; Protective Agents ; Respiratory System Agents ; Vasodilator Agents
Molecular Formula of 1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-,(3R,4aR,5S,6S,6aS,10S,10aR,10bS)- (CAS NO.66575-29-9 ): C₂₂H₃₄O₇
Molecular Weight: 410.5012
Molecular Structure:

Melting Point: 282-232 °C
H bond acceptors: 7
H bond donors: 3
Freely Rotating Bonds: 6
Polar Surface Area: 80.29 Å²
Index of Refraction: 1.551
Molar Refractivity: 105.82 cm³
Molar Volume: 331.3 cm³
Surface Tension: 51.4 dyne/cm
Density of 1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-,(3R,4aR,5S,6S,6aS,10S,10aR,10bS)- (CAS NO.66575-29-9 ): 1.23 g/cm³
Flash Point: 171.8 °C
Enthalpy of Vaporization: 91.23 kJ/mol
Boiling Point: 519.9 °C at 760 mmHg
Vapour Pressure: 5.56E-13 mmHg at 25°C

Forskolin Uses

1H-Naphtho[2,1-b]pyran-1-one,5-(acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-,(3R,4aR,5S,6S,6aS,10S,10aR,10bS)- (CAS NO.66575-29-9 ) is used as possessing vasodilating and cardiostimulatory properties.

Forskolin Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	68mg/kg (68mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Journal of Ethnopharmacology. Vol. 3, Pg. 1, 1981.
mouse	LD50	oral	3100mg/kg (3100mg/kg)		Medicinal Research Reviews. Vol. 3, Pg. 201, 1983.
rat	LD50	intraperitoneal	92mg/kg (92mg/kg)		Journal of Medicinal Chemistry. Vol. 31, Pg. 1872, 1988.
rat	LD50	oral	2550mg/kg (2550mg/kg)		Medicinal Research Reviews. Vol. 3, Pg. 201, 1983.

Forskolin Safety Profile

Hazard Codes: Harmful Xn
Risk Statements: 21
R21: Harmful in contact with skin.
Safety Statements: 22-36/37
S22: Do not breathe dust.
S36/37: Wear suitable protective clothing and gloves.
WGK Germany :3
RTECS: QL6150000
F: 10-21

Product Name

FORSKOLIN

Synthetic route

Forskolin Chemical Properties

Forskolin Uses

Forskolin Toxicity Data With Reference

Forskolin Safety Profile

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