Absolute structure and total synthesis of lipogrammistin-A, a lipophilic ichthyotoxin of the soapfish

被引：15

作者：

Onuki, H

Ito, K

Kobayashi, Y

Matsumori, N

Tachibana, K

Fusetani, N

机构：

[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

[2] Univ Tokyo, Grad Sch Agr & Life Sci, Lab Aquat Nat Prod Chem, Bunkyo Ku, Tokyo 1130032, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 12期

关键词：

D O I：

10.1021/jo9722461

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lipogrammistin-A (Ib) was isolated as an ichthyotoxic and hemolytic constituent of the skin mucus of the grammistid fish Aulacocephalus temmincki. Its absolute stereochemistry was established by chemical degradation and total synthesis. The stereochemistry of the 2-methylbutyryl moieties attached to N9 and N15 was determined to be S by HPLC analysis of a diastereomeric derivative. The stereochemistry of the remaining C4 position was elucidated to be S by a total synthesis of the two diastereomers (4S)- and (4R)-1.

引用

页码：3925 / 3932

页数：8

共 25 条

[11]

NAIR MSR, 1988, HDB NATURAL TOXINS, V3, P211

[12] STRUCTURE OF LIPOGRAMMISTIN-A, A LIPOPHILIC ICHTHYOTOXIN SECRETED BY THE SOAPFISH DIPLOPRION-BIFASCIATUM [J].