Total synthesis and adjuvant activity of all stereoisomers of pinellic acid

被引：30

作者：

Shirahata, T

Sunazuka, T

Yoshida, K

Yamamoto, D

Harigaya, Y

Nagai, T

Kiyohara, H

Yamada, H

Kuwajima, I

Omura, S ^{[1
]}

机构：

[1] Kitasato Univ, Kitasato Inst Life Sci, Tokyo 1088641, Japan

[2] Kitasato Univ, Sch Pharmaceut Sci, Tokyo 1088641, Japan

[3] Kitasato Inst, Tokyo 1088641, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2003年 / 13卷 / 05期

关键词：

D O I：

10.1016/S0960-894X(02)01069-7

中图分类号：

R914 [药物化学];

学科分类号：

100701 [药物化学];

摘要：

Pinellic acid is a novel and potentially useful oral adjuvant when used in conjunction with intranasal inoculation of influenza HA vaccines. All stereoisomers of pinellic acid have been synthesized via regioselective asymmetric dihydroxylation, regioselective inversion, and stereoselective reduction, and their adjuvant activities were characterized. Among this series of isomers, 9S, 12S, 13S compound has the most potent adjuvant activity. Structure-activity relationships are discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：937 / 941

页数：5

共 7 条

[1]

[Anonymous], VIROLOGY

[2]

CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].