Total synthesis of brevenal

Hiroyoshi Takamura, Yuji Yamagami, Takayuki Kishi, Shigetoshi Kikuchi, Yuichi Nakamura, Isao Kadota, Yoshinori Yamamoto

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The convergent total synthesis of brevenal, a non-toxic brevetoxin antagonist, has been achieved.The ABC ring segment and the E ring precursor were connected by the intramolecular allylation followed by ring-closing metathesis to furnish the pentacyclic ether compound.An alternative route to the key synthetic intermediate, a pentacyclic ether core, was also examined.The right-and left-hand side chains were introduced by Wittig and HornereWadswortheEmmons reactions, respectively, to furnish brevenal (1).

Original languageEnglish
Pages (from-to)5329-5344
Number of pages16
JournalTetrahedron
Volume66
Issue number29
DOIs
Publication statusPublished - Jul 17 2010

Keywords

  • Brevenal
  • Intramolecular allylation
  • Marine polycyclic ether
  • Ring-closing metathesis
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Takamura, H., Yamagami, Y., Kishi, T., Kikuchi, S., Nakamura, Y., Kadota, I., & Yamamoto, Y. (2010). Total synthesis of brevenal. Tetrahedron, 66(29), 5329-5344. https://doi.org/10.1016/j.tet.2010.05.069