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A convenient synthesis of 2 beta,3 alpha-dihydroxyurs-12-en-28-oic acid as a natural diastereoisomer of corosolic acid

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Indexed by:期刊论文

Date of Publication:2013-07-01

Journal:CHINESE CHEMICAL LETTERS

Included Journals:SCIE、ISTIC

Volume:24

Issue:7

Page Number:617-618

ISSN No.:1001-8417

Key Words:2 beta,3 alpha-Dihydroxyurs-12-en-28-oic acid; Ursolic acid; Glycogen phosphorylase; Corosolic acid

Abstract:2 beta,3 alpha-Dihydroxyurs-12-en-28-oic acid (6) is a naturally occurring diastereoisomer of corosolic acid with glycogen phosphorylase inhibitory activity. A new strategy for the semi-synthesis of 6 was developed. Using the commercially available ursolic acid (1) as the starting materials, 6 was synthesized through five facile reactions with a high stereoselectivity and an overall yield of 47.3%. The structure of 6 was confirmed by optical rotation, ESI-MS, H-1 NMR and C-13 NMR data. (C) 2013 Shi-Sheng Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

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