Total synthesis of brevetoxin B

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2 Citations (Scopus)

Abstract

Brevetoxin B was isolated from the red tide organism Karenia brevis in 1981 as the first example of marine polycyclic ethers. This compound shows potent neurotoxicity, by binding to sodium channels, causing massive fish kills and human health problems. Since further biological studies are hampered by the limited availability from nature, chemical synthesis has been the sole realistic way to obtain sufficient amounts of brevetoxin B. Moreover, the huge molecular architecture is a particularly attractive target for synthetic chemists. In this account, we describe the highly convergent total synthesis of brevetoxin B based on our methodology, including intramolecular allylation and subsequent ring-closing metathesis.

Original languageEnglish
Pages (from-to)430-437
Number of pages8
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume65
Issue number5
Publication statusPublished - May 1 2007

Keywords

  • Brevetoxin B
  • Intramolecular allylation
  • Polycyclic ethers
  • Ring-closing metathesis
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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