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

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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.

Original languageEnglish
Pages (from-to)617-627
Number of pages11
JournalHeterocycles
Volume74
Issue numberC
Publication statusPublished - Dec 31 2007

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Kadota, I., Abe, T., Ishitsuka, Y., Touchy, A. S., Nagata, R., & Yamamoto, Y. (2007). Formal total synthesis of hemibrevetoxin B via the intramolecular allylation followed by ring-closing metathesis. Heterocycles, 74(C), 617-627.