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

doi:10.1021/jo9722461

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 journal › Article › peer-review

14 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 language	English
Pages (from-to)	3925-3932
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	63
Issue number	12
DOIs	https://doi.org/10.1021/jo9722461
Publication status	Published - Jun 12 1998
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo9722461

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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.",

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T1 - Absolute structure and total synthesis of lipogrammistin-A, a lipophilic ichthyotoxin of the soapfish

AU - Onuki, Hiroyuki

AU - Ito, Kei

AU - Kobayashi, Yoshimasa

AU - Matsumori, Nobuaki

AU - Tachibana, Kazuo

AU - Fusetani, Nobuhiro

PY - 1998/6/12

Y1 - 1998/6/12

N2 - 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.

AB - 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.

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ER -

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

Abstract

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