Improved synthesis of the A-G ring segment of brevetoxin B

Isao Kadota, Hiroki Nishii, Hiroki Ishioka, Hiroyoshi Takamura, Yoshinori Yamamoto

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

An efficient synthesis of the A-G ring segment 2, a key intermediate for the total synthesis of brevetoxin B (1), was achieved in 37 steps and 5.0% overall yield. The intramolecular allylation of the O,S-acetal 22, prepared from the ABC ring segment 15 and the FG ring segment 17, was carried out using AgOTf as a Lewis acid to give the desired compound 23, predominantly. Ring-closing metathesis of 23 with the Grubbs catalyst 12 afforded the heptacyclic ether 25. Selective hydrogenation of the E ring olefin of 25 was performed by diimide reduction to afford 2.

Original languageEnglish
Pages (from-to)4183-4187
Number of pages5
JournalJournal of Organic Chemistry
Volume71
Issue number11
DOIs
Publication statusPublished - May 26 2006
Externally publishedYes

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Allylation
Lewis Acids
Acetals
Alkenes
Ether
Hydrogenation
Catalysts
brevetoxin B
22-amino-23,24-bisnor-5-cholen-3-ol

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Improved synthesis of the A-G ring segment of brevetoxin B. / Kadota, Isao; Nishii, Hiroki; Ishioka, Hiroki; Takamura, Hiroyoshi; Yamamoto, Yoshinori.

In: Journal of Organic Chemistry, Vol. 71, No. 11, 26.05.2006, p. 4183-4187.

Research output: Contribution to journalArticle

Kadota, Isao ; Nishii, Hiroki ; Ishioka, Hiroki ; Takamura, Hiroyoshi ; Yamamoto, Yoshinori. / Improved synthesis of the A-G ring segment of brevetoxin B. In: Journal of Organic Chemistry. 2006 ; Vol. 71, No. 11. pp. 4183-4187.
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