Total synthesis of pinellic acid, a potent oral adjuvant for nasal influenza vaccine. Determination of the relative and absolute configuration

被引：27

作者：

Sunazuka, T

Shirahata, T

Yoshida, K

Yamamoto, D

Harigaya, Y

Nagai, T

Kiyohara, H

Yamada, H

Kuwajima, I

Omura, S ^{[1
]}

机构：

[1] Kitasato Inst, Oriental Med Res Ctr, Minato Ku, Tokyo 1088641, Japan

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

[3] Kitasato Univ, Kitasato Inst Life Sci, Minato Ku, Tokyo 1088641, Japan

[4] Japan Sci & Technol Corp, CREST, Minato Ku, Tokyo 1088641, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 07期

关键词：

adjuvant; 10E-9,12,13-trihydroxyoctadecenoic acid; asymmetric dihydroxylation; BINAL-H;

D O I：

10.1016/S0040-4039(01)02348-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Pinellic acid (1), isolated from a medicinal plant Pinelliae tuber. has potent adjuvant activity. The absolute configuration of pinellic acid was expected by derivatization of this compound and CD exciton chirality method. A convergent synthetic route to pinellic acid has been developed via regioselective asymmetric dihydroxylation and stereoselective reduction. The absolute configuration of pinellic acid was determined to be 9S,12S,13S, by comparing with the spectra data of natural and synthetic compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1265 / 1268

页数：4

共 19 条

[1]

COLIN DF, 1983, BIOCHIM BIOPHYS ACTA, V754, P57

[2]

NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].