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

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3925-3932
Number of pages8
JournalJournal of Organic Chemistry
Volume63
Issue number12
DOIs
Publication statusPublished - Jun 12 1998
Externally publishedYes

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Stereochemistry
Fish
Skin
Derivatives
Degradation
lipogrammistin A

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Absolute structure and total synthesis of lipogrammistin-A, a lipophilic ichthyotoxin of the soapfish. / Onuki, Hiroyuki; Ito, Kei; Kobayashi, Yoshimasa; Matsumori, Nobuaki; Tachibana, Kazuo; Fusetani, Nobuhiro.

In: Journal of Organic Chemistry, Vol. 63, No. 12, 12.06.1998, p. 3925-3932.

Research output: Contribution to journalArticle

Onuki, Hiroyuki ; Ito, Kei ; Kobayashi, Yoshimasa ; Matsumori, Nobuaki ; Tachibana, Kazuo ; Fusetani, Nobuhiro. / Absolute structure and total synthesis of lipogrammistin-A, a lipophilic ichthyotoxin of the soapfish. In: Journal of Organic Chemistry. 1998 ; Vol. 63, No. 12. pp. 3925-3932.
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