100348-38-7

Basic information

• Product Name: (-)-isodesoxypodophyllotoxine
• CAS NO: 100348-38-7
• Molecular Weight: 398.412
• Mol File: 100348-38-7.mol
• Article Data: 41

Chemical Properties

• CAS DataBase Reference: (-)-isodesoxypodophyllotoxine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-isodesoxypodophyllotoxine(100348-38-7)
• EPA Substance Registry System: (-)-isodesoxypodophyllotoxine(100348-38-7)

Safety Data

• Hazardous Substances Data: 100348-38-7(Hazardous Substances Data)

Upstream product

• 137047-04-2 (Z)-4-(2-Bromo-4,5-methylenedioxybenzyl)-3-(3,4,5-trimethoxybenzylidene)dihydro-2(3H)-furanone 
• 120-57-0 piperonal 
• 74879-22-4 6-bromobenzo-1,3-dioxole-5-carboxaldehyde dimethyl acetal 
• 1254-07-5 7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 137047-03-1 trans-4-(2-Bromo-4,5-methylenedioxybenzyl)-3-(α-chloro-3,4,5-trimethoxybenzyl)dihydro-2(3H)-furanone 
• 82792-83-4 -3,4-methylenedioxybenzyl alcohol 
• 82792-85-6 5,6-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,3-dihydrobenzothiophene 
• 82792-81-2 1-(3,4,5-trimethoxyphenyl)-5,6-methylenedioxy-1,3-dihydrobenzothiophene-2,2-dioxide 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 6642-34-8 6-bromopiperonyl alcohol 
• 82792-87-8 (6-bromobenzo[d][1,3]dioxol-5-yl)methanethiol 
• 82792-89-0 dimethyl 6,7-methylenedioxy-r-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-c-2,c-3-dicarboxylate 
• 1254-07-5 (5S,6S,7R)-7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 

Downstream Products

• 78215-95-9 desoxypodophyllinic acid ethyl ester 
• 514223-10-0 Methanesulfonic acid (5R,6R,7R)-7-methoxymethoxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester 
• 514223-12-2 (5R,6R,7R)-7-Methoxymethoxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester 
• 514223-09-7 [(5R,6R,7R)-7-Methoxymethoxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-yl]-methanol 
• 514223-13-3 (5R,6R,7R)-7-Methoxymethoxymethyl-6-methyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole 
• 514223-14-4 [(6R,7R,8R)-7-Methyl-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-yl]-methanol 

Relevant articles and documents

BIOSYNTHETIC RELATIONSHIP OF ARYLTETRALIN LACTONE LIGNANS TO DIBENZYLBUTYROLACTONE LIGNANS

Key Word Index - Podophyllum hexandrum; Podophyllaceae; lignans; aryltetralin; dibenzylbutyrolactone; biosynthesis; podophyllotoxin. Feeding experiments in Podophyllum hexandrum plants have shown that the dibenzylbutyrolactone lignan yatein is a satisfactory precursor of the aryltetralin lignan podophyllotoxin.The corresponding cis isomer of yatein was also incorporated, but to a lesser extent, and probably via yatein.Podorhizol, epipodorhizol and anhydropodorhizol were not incorporated into podophyllotoxin, despite the demonstrated presence of both podorhizol and anhydropodorhizol in P. hexandrum plants.A biosynthetic sequence from yatein to podophyllotoxin via a key quinonemethide intermediate is proposed.This intermediate is probably also the precursor of both podorhizol and anhydropodorhizol.Matairesinol is proposed as the branchpoint compound to the trimethoxy and hydroxydimethoxy series of aryltetralin lignans in Podophyllum.Labelling patterns in podophyllotoxin and 4'-demethylpodophyllotoxin derived from methionine support this suggestion.

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Chemoenzymatic Total Synthesis of Deoxy-, epi-, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones

Podophyllotoxin is probably the most prominent representative of lignan natural products. Deoxy-, epi-, and podophyllotoxin, which are all precursors to frequently used chemotherapeutic agents, were prepared by a stereodivergent biotransformation and a biocatalytic kinetic resolution of the corresponding dibenzylbutyrolactones with the same 2-oxoglutarate-dependent dioxygenase. The reaction can be conducted on 2 g scale, and the enzyme allows tailoring of the initial, “natural” structure and thus transforms various non-natural derivatives. Depending on the substitution pattern, the enzyme performs an oxidative C?C bond formation by C?H activation or hydroxylation at the benzylic position prone to ring closure.

Divergent Asymmetric Syntheses of Podophyllotoxin and Related Family Members via Stereoselective Reductive Ni-Catalysis

A nickel-catalyzed reductive cascade approach to the efficient construction of diastereodivergent cores embedded in podophyllum lignans is developed for the first time. Their gram-scale access paved the way for unified syntheses of naturally occurring podophyllotoxin and other members.