A spontaneous bicyclization facilitates a synthesis of (-)-hispidospermidin

Junko Tamiya, Erik J. Sorensen

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

A concise, enantiospecific synthesis of the phospholipase C inhibitor (-)-hispidospermidin (1) has been achieved by approximating the architecture of a reactive intermediate that may lie on the biosynthetic pathway leading to this natural product. Two compounds derived from (R)-(+)-pulegone were joined by a highly diastereoselective carbonyl addition. A proximity-facilitated, acid-induced bicyclization of spiro[4.5]deca-1,7-diene 29 gave rise to the tetracyclic framework of 1 and was the key transformation in this synthesis.

Original languageEnglish (US)
Pages (from-to)6921-6932
Number of pages12
JournalTetrahedron
Volume59
Issue number35
DOIs
StatePublished - Aug 25 2003
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • Biomimetic synthesis
  • Hispidospermidin
  • Proximity
  • π-cyclization

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