An improved synthesis of (-)-brevisamide, a marine monocyclic ether amide of dinoflagellate origin

Ryosuke Tsutsumi, Takefumi Kuranaga, Jeffrey L.C. Wright, Daniel G. Baden, Emiko Ito, Masayuki Satake, Kazuo Tachibana

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

An improved synthesis of (-)-brevisamide a marine cyclic ether isolated from the red-tide dinoflagellate Karenia brevis was achieved. The ether ring portion was constructed from an unsaturated lactone, which was prepared enantioselectively via an Evans aldol reaction and one-pot lactonization in the presence of excessive base after an Ando reaction. The ether ring and a dienol side chain fragment were connected via Suzuki-Miyaura coupling.

Original languageEnglish
Pages (from-to)6775-6782
Number of pages8
JournalTetrahedron
Volume66
Issue number34
DOIs
Publication statusPublished - 2010 Aug 21
Externally publishedYes

Keywords

  • Cyclic ether
  • Dinoflagellate origin
  • One-pot lactonization
  • Suzuki-Miyaura coupling

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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