Synthesis of (±)-epiisopodophyllotoxin
- 1 March 1983
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 61 (3) , 573-575
- https://doi.org/10.1139/v83-101
Abstract
The synthesis of (±)-epiisopodophyllotoxin commencing with 6-bromopiperonal dimethyl acetal is described. The carbon skeleton of isoepipodophyllotoxin was assembled via a Diels–Alder reaction between the hydroxyquinodimethane generated photochemically from 6-(3′,4′,5′-trimethoxybenzyl)-piperonal, obtained from the bromoacetal above, and dimethyl fumarate. This Diels–Alder adduct was converted in five steps into the title compound. The overall yield for the seven steps was 15%.This publication has 1 reference indexed in Scilit:
- Conformational analysis of podophyllotoxin and its congeners. Structure-activity relationship in microtubule assemblyJournal of Medicinal Chemistry, 1979