ENANTIOSELECTIVE TOTAL SYNTHESES AND STEREOCHEMICAL STUDIES OF ALL 4 STEREOISOMERS OF YINGZHAOSU-C

Authors
XU XX DONG HQ
Citation
Xx. Xu et Hq. Dong, ENANTIOSELECTIVE TOTAL SYNTHESES AND STEREOCHEMICAL STUDIES OF ALL 4 STEREOISOMERS OF YINGZHAOSU-C, Journal of organic chemistry, 60(10), 1995, pp. 3039-3044
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
10
Year of publication
1995
Pages
3039 - 3044
Database
ISI
SICI code
0022-3263(1995)60:10<3039:ETSASS>2.0.ZU;2-O
Abstract
The enantioselective total syntheses and the stereochemistry of all fo ur stereoisomers of yingzhaosu C, an antimalarial peroxy-containing se squiterpene isolated from yingzhao [Artabotrys uncinatus (L.) Merr.], are described. The key to the syntheses was the combination of Sharple ss asymmetric epoxidation and the intramolecular nucleophilic epoxy-op ening with a benzylic peroxy group to construct the 1,2-dioxane skelet on. The configurations of the 1,2-dioxanes in four stereoisomers were assigned by spectroscopy and chemical transformation.