17245-16-8

Basic information

• Product Name: 8H-[1,3]Dioxolo[6,7][2]benzopyrano[3,4-c]indol- 8-ol,3,4,4a,5,6,6a-hexahydro-3-methoxy-5- methyl-,(3R,4aS,6aR,8R,13bS)-
• CAS NO: 17245-16-8
• Mol File: 17245-16-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 8H-[1,3]Dioxolo[6,7][2]benzopyrano[3,4-c]indol- 8-ol,3,4,4a,5,6,6a-hexahydro-3-methoxy-5- methyl-,(3R,4aS,6aR,8R,13bS)- (CAS DataBase Reference)
• NIST Chemistry Reference: 8H-[1,3]Dioxolo[6,7][2]benzopyrano[3,4-c]indol- 8-ol,3,4,4a,5,6,6a-hexahydro-3-methoxy-5- methyl-,(3R,4aS,6aR,8R,13bS)- (17245-16-8)
• EPA Substance Registry System: 8H-[1,3]Dioxolo[6,7][2]benzopyrano[3,4-c]indol- 8-ol,3,4,4a,5,6,6a-hexahydro-3-methoxy-5- methyl-,(3R,4aS,6aR,8R,13bS)- (17245-16-8)

Safety Data

• Hazardous Substances Data: 17245-16-8(Hazardous Substances Data)

Upstream product

• 65673-83-8 5-(chloromethyl)-6-iodobenzo[d][1,3]dioxole 
• 495-76-1 piperonol 
• 69048-76-6 6-iodo-1,3-benzodioxole-5-methanol 
• 74120-53-9 (3α,3aα,6α,7aα)-3a,6,7,7a-tetrahydro-6-methoxy-1-methyl-3a-<3,4-(methylenedioxy)phenyl>-3-indolinol 
• 74120-48-2 4-(bromoacetyl)-5-methoxy-4-<3,4-(methylenedioxy)phenyl>-cyclohex-2-en-1-one 
• 74120-58-4 (3aα,7aα)-3a,6,7,7a-tetrahydro-1-methyl-6-hydroxy-3a-<3,4-(methylenedioxy)phenyl>-3-indolinone 
• 74120-57-3 (3aα,7aα)-3a,6,7,7a-tetrahydro-1-methyl-6-hydroxy-3a-<3,4-(methylenedioxy)phenyl>-3-indolinone 
• 74120-52-8 (3aα,6α,7aα)-3a,6,7,7a-tetrahydro-6-methoxy-1-methyl-3a-<3,4-(methylenedioxy)phenyl>-3-indolinone 
• 74120-50-6 (3aα,7aα)-3a,6,7,7a-tetrahydro-1-methyl-3a-<3,4-(methylenedioxy)phenyl>-6-oxo-3-indolinone 
• 74120-53-9 (3aR,6R,7aR)-3a-Benzo[1,3]dioxol-5-yl-6-methoxy-1-methyl-2,3,3a,6,7,7a-hexahydro-1H-indol-3-ol 
• 86116-85-0 O-methyl-6a-epipretazettine 
• 74165-11-0 (3α,3aα,6α,7aα)-3a,6,7,7a-tetrahydro-3a-<2-(hydroxymethyl)-4,5-(methylenedioxy)phenyl>-6-methoxy-1-methyl-3-indolinol 
• 74-88-4 methyl iodide 
• 2568-36-7 6,6-dibromobicylo[3.1.0]hexane 

Downstream Products

• 507-79-9 tazettine 
• 545-16-4 (4aS)-3t-methoxy-5-methyl-(4ar,13btC¹)-4,4a,5,6-tetrahydro-3H,8H-[1,3]dioxolo[4',5':6,7]isochromeno[3,4-c]indol-6at-ol 
• 1936-81-8 N-Desmethyl-macronin 
• 1936-81-8 N-Desmethyl-3-epi-macronin 
• 1936-80-7 jonquailine 

Relevant articles and documents

Application of Electrocyclic Ring-Opening and Desymmetrizing Nucleophilic Trappings of meso-6,6-Dibromobicyclo[3.1.0]hexanes to Total Syntheses of Crinine and Haemanthamine Alkaloids

The thermally induced electrocyclic ring-opening of C2-symmetric (meso) 6,6-dibromobicyclo[3.1.0]hexanes such as 10 in the presence of the chiral, nonracemic 1°-amine 28 afforded a ca. 1:1 mixture of the diastereoisomeric and chromatographically separable 1-amino-2-bromo-2-cyclohexenes 37 (42%) and 38 (45%). Each of these was elaborated over 13 steps, including Suzuki-Miyaura cross-coupling, radical cyclization, and Pictet-Spengler reactions, into (-)- or (+)-crinane (1 or ent-1, respectively). Variations on these protocols were applied to the total syntheses of (+)- and (-)-11-hydroxyvattitine [(+)- and (-)-3], (+)- and (-)-bulbispermine [(+)- and (-)-4], (+)- and (-)-haemanthamine [(+)- and (-)-5], (+)- and (-)-pretazettine [(+)- and (-)-6], and (+)- and (-)-tazettine [(+)- and (-)-7] as well as (±)-hamayne [(±)-8] and (±)-apohaemanthamine [(±)-9]. A number of these alkaloids were synthesized for the first time.

First Asymmetric Total Syntheses of (+)-Crinamine, (-)-Haemanthidine, and (+)-Pretazettine

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Phenolic Oxidative Coupling with Hypervalent Iodine. A Synthesis of 6a-Epipretazettine

6a-Epipretazettine was synthesized in seven steps from piperonal and synephrine.Intramolecular, monophenolic, oxidative coupling of a functionalized benzylic acetal, employing benzene as oxidant, gave a spirodienone in 13 percent yield.Subsequent deprotection of the secondary amine was followed by spontaneous closure to a tetracyclic pyrrolidine possessing an all-cis ring fusion.This substance was reduced with diisobutylaluminum hydride, and the resulting alcohol was transformed, via methanolysis of the corresponding mesylate, to O-methyl-6a-epipretazettine.Acidic hydrolysis of the latter yielded 6a-epipretazettine, identical with material previously obtained by Danishefsky.