Formal total synthesis of hemibrevetoxin B via the intramolecular allylation followed by ring-closing metathesis

Isao Kadota; Takashi Abe; Yukako Ishitsuka; Abeda S. Touchy; Ryoko Nagata; Yoshinori Yamamoto

doi:10.3987/com-07-s(w)39

Formal total synthesis of hemibrevetoxin B via the intramolecular allylation followed by ring-closing metathesis

Isao Kadota, Takashi Abe, Yukako Ishitsuka, Abeda S. Touchy, Ryoko Nagata, Yoshinori Yamamoto

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

5 Citations (Scopus)

Abstract

A formal total synthesis of hemibrevetoxin B (1) is described. Intramolecular allylation of α-chloroacetoxy ether 10, prepared from carboxylic acid 11 and alcohol 12, was carried out with MgBr₂·OEt₂ to give 27. Ring-closing metathesis of 27 furnished tetracycle 29, which was converted to a known synthetic intermediate 9, to complete a formal total synthesis of 1.

Original language	English
Pages (from-to)	617-627
Number of pages	11
Journal	Heterocycles
Volume	74
Issue number	C
DOIs	https://doi.org/10.3987/com-07-s(w)39
Publication status	Published - Dec 31 2007

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "A formal total synthesis of hemibrevetoxin B (1) is described. Intramolecular allylation of α-chloroacetoxy ether 10, prepared from carboxylic acid 11 and alcohol 12, was carried out with MgBr2·OEt2 to give 27. Ring-closing metathesis of 27 furnished tetracycle 29, which was converted to a known synthetic intermediate 9, to complete a formal total synthesis of 1.",

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T1 - Formal total synthesis of hemibrevetoxin B via the intramolecular allylation followed by ring-closing metathesis

AU - Kadota, Isao

AU - Abe, Takashi

AU - Ishitsuka, Yukako

AU - Touchy, Abeda S.

AU - Nagata, Ryoko

AU - Yamamoto, Yoshinori

PY - 2007/12/31

Y1 - 2007/12/31

N2 - A formal total synthesis of hemibrevetoxin B (1) is described. Intramolecular allylation of α-chloroacetoxy ether 10, prepared from carboxylic acid 11 and alcohol 12, was carried out with MgBr2·OEt2 to give 27. Ring-closing metathesis of 27 furnished tetracycle 29, which was converted to a known synthetic intermediate 9, to complete a formal total synthesis of 1.

AB - A formal total synthesis of hemibrevetoxin B (1) is described. Intramolecular allylation of α-chloroacetoxy ether 10, prepared from carboxylic acid 11 and alcohol 12, was carried out with MgBr2·OEt2 to give 27. Ring-closing metathesis of 27 furnished tetracycle 29, which was converted to a known synthetic intermediate 9, to complete a formal total synthesis of 1.

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JO - Heterocycles

JF - Heterocycles

IS - C

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Formal total synthesis of hemibrevetoxin B via the intramolecular allylation followed by ring-closing metathesis

Abstract

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