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

Hiroyuki Onuki, Kei Ito, Yoshimasa Kobayashi, Nobuaki Matsumori, Kazuo Tachibana, Nobuhiro Fusetani

研究成果: Contribution to journalArticle査読

13 被引用数 (Scopus)

抄録

Lipogrammistin-A (1b) 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.

本文言語英語
ページ(範囲)3925-3932
ページ数8
ジャーナルJournal of Organic Chemistry
63
12
DOI
出版ステータス出版済み - 6 12 1998
外部発表はい

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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