AN EFFICIENT STEREOCONTROLLED SYNTHESIS OF (-)-10-EPI-5-BETA,11-DIHYDROXYEUDESMANE AND (-)-4,10-EPI-5-BETA,11-DIHYDROXYEUDESMANE

Authors
XIONG ZM ZHOU G YANG J CHEN YG LI YL
Citation
Zm. Xiong et al., AN EFFICIENT STEREOCONTROLLED SYNTHESIS OF (-)-10-EPI-5-BETA,11-DIHYDROXYEUDESMANE AND (-)-4,10-EPI-5-BETA,11-DIHYDROXYEUDESMANE, Tetrahedron : asymmetry, 9(9), 1998, pp. 1525-1530
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
9
Year of publication
1998
Pages
1525 - 1530
Database
ISI
SICI code
0957-4166(1998)9:9<1525:AESSO(>2.0.ZU;2-M
Abstract
A concise and efficient synthesis of (-)-10-epi-5 beta, 11-dihydroxyeu desmane 1 and (-)-4,10-epi-5 beta, 11-dihydroxyeudesmane 2, via (-)-10 -epi-gamma-eudesmol 5, was accomplished starting from (+)-dihydrocarvo ne. The salient feature of our synthesis is the utilization of substra te-directable epoxidation and homogeneous hydrogenation to control the stereochemistry at the C-4 and C-5 positions of the title compounds. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.