AN ASYMMETRIC-SYNTHESIS OF (-)-DEOXYPODOPHYLLOTOXIN

Authors
BOGUCKI DE CHARLTON JL
Citation
De. Bogucki et Jl. Charlton, AN ASYMMETRIC-SYNTHESIS OF (-)-DEOXYPODOPHYLLOTOXIN, Journal of organic chemistry, 60(3), 1995, pp. 588-593
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
3
Year of publication
1995
Pages
588 - 593
Database
ISI
SICI code
0022-3263(1995)60:3<588:AAO(>2.0.ZU;2-2
Abstract
Diels-Alder cycloaddition between the fumarate of methyl (S)-mandelate (22) and alpha-hydroxy-alpha-aryl-o-quinodimethane 21 produces an end o cycloadduct (23) in 58% yield. The preparation of the precursor to o -quinodimethane 21 and the conversion of cycloadduct 23 to optically p ure (-)-deoxypodophyllotoxin (1) is described.