A convergent synthesis of the trans-fused hexahydrooxonine ring system and reproduction of conformational behavior shown by ring F of ciguatoxin

Masayuki Inoue; Makoto Sasaki; Kazuo Tachibana

doi:10.1016/S0040-4020(99)00620-1

A convergent synthesis of the trans-fused hexahydrooxonine ring system and reproduction of conformational behavior shown by ring F of ciguatoxin

Masayuki Inoue, Makoto Sasaki, Kazuo Tachibana

Research output: Contribution to journal › Article › peer-review

44 Citations (Scopus)

Abstract

A new strategy for the construction of the fused hexahydrooxonine ring system has been developed. The present synthesis involves an intramolecular reaction of γ-alkoxyallylsilane with acetal to form an O-linked oxacycle and a SmI₂-mediated intramolecular Reformatsky reaction for constructing an oxonane ring as the key steps. Thermodynamic behavior of the trans-fused hexahydrooxonine ring was clarified for the first time and the conformational alternation was reproduced in the 6-9-6 tricyclic model compound 1 as was observed for that in the ciguatoxin molecule (ring F).

Original language	English
Pages (from-to)	10949-10970
Number of pages	22
Journal	Tetrahedron
Volume	55
Issue number	36
DOIs	https://doi.org/10.1016/S0040-4020(99)00620-1
Publication status	Published - 1999 Sept 3
Externally published	Yes

Keywords

Conformation
Medium-ring heterocycles
Polyethers
Reformatsky reactions

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(99)00620-1

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title = "A convergent synthesis of the trans-fused hexahydrooxonine ring system and reproduction of conformational behavior shown by ring F of ciguatoxin",

abstract = "A new strategy for the construction of the fused hexahydrooxonine ring system has been developed. The present synthesis involves an intramolecular reaction of γ-alkoxyallylsilane with acetal to form an O-linked oxacycle and a SmI2-mediated intramolecular Reformatsky reaction for constructing an oxonane ring as the key steps. Thermodynamic behavior of the trans-fused hexahydrooxonine ring was clarified for the first time and the conformational alternation was reproduced in the 6-9-6 tricyclic model compound 1 as was observed for that in the ciguatoxin molecule (ring F).",

keywords = "Conformation, Medium-ring heterocycles, Polyethers, Reformatsky reactions",

author = "Masayuki Inoue and Makoto Sasaki and Kazuo Tachibana",

note = "Funding Information: Acknowledgment: This work was financially supported in part by a Grant-in-Aid for Scientific Research on Priority Area No. 08245103 from the Ministry of Education, Science, Sports and Culture, of Japan to M. S. and a fellowship to M. I. from the Japan Society for the Promotion of Science for Young Scientists. We thank Professor M. Murata, Osaka University, for the valuable discussions and advice throughout this study.",

year = "1999",

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doi = "10.1016/S0040-4020(99)00620-1",

language = "English",

volume = "55",

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journal = "Tetrahedron",

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T1 - A convergent synthesis of the trans-fused hexahydrooxonine ring system and reproduction of conformational behavior shown by ring F of ciguatoxin

AU - Inoue, Masayuki

AU - Sasaki, Makoto

AU - Tachibana, Kazuo

N1 - Funding Information: Acknowledgment: This work was financially supported in part by a Grant-in-Aid for Scientific Research on Priority Area No. 08245103 from the Ministry of Education, Science, Sports and Culture, of Japan to M. S. and a fellowship to M. I. from the Japan Society for the Promotion of Science for Young Scientists. We thank Professor M. Murata, Osaka University, for the valuable discussions and advice throughout this study.

PY - 1999/9/3

Y1 - 1999/9/3

N2 - A new strategy for the construction of the fused hexahydrooxonine ring system has been developed. The present synthesis involves an intramolecular reaction of γ-alkoxyallylsilane with acetal to form an O-linked oxacycle and a SmI2-mediated intramolecular Reformatsky reaction for constructing an oxonane ring as the key steps. Thermodynamic behavior of the trans-fused hexahydrooxonine ring was clarified for the first time and the conformational alternation was reproduced in the 6-9-6 tricyclic model compound 1 as was observed for that in the ciguatoxin molecule (ring F).

AB - A new strategy for the construction of the fused hexahydrooxonine ring system has been developed. The present synthesis involves an intramolecular reaction of γ-alkoxyallylsilane with acetal to form an O-linked oxacycle and a SmI2-mediated intramolecular Reformatsky reaction for constructing an oxonane ring as the key steps. Thermodynamic behavior of the trans-fused hexahydrooxonine ring was clarified for the first time and the conformational alternation was reproduced in the 6-9-6 tricyclic model compound 1 as was observed for that in the ciguatoxin molecule (ring F).

KW - Conformation

KW - Medium-ring heterocycles

KW - Polyethers

KW - Reformatsky reactions

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U2 - 10.1016/S0040-4020(99)00620-1

DO - 10.1016/S0040-4020(99)00620-1

M3 - Article

AN - SCOPUS:0033520269

SN - 0040-4020

VL - 55

SP - 10949

EP - 10970

JO - Tetrahedron

JF - Tetrahedron

IS - 36

ER -

A convergent synthesis of the trans-fused hexahydrooxonine ring system and reproduction of conformational behavior shown by ring F of ciguatoxin

Abstract

Keywords

ASJC Scopus subject areas

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