First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin

Takahiro Suzuki, Kenji Usui, Yoshiharu Miyake, Michio Namikoshi, Masahisa Nakada

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

(Equation presented) The first total synthesis of (+)-phomopsidin has been achieved via a diastereoselective transannular Diels-Alder (TADA) reaction. Key steps in the synthesis include diastereoselective ynone reduction with (-)-α-pinene and 9-BBN, macrocyclization by E-selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction, as well as carbometalation under Wipf's conditions, followed by HWE reaction at low temperature to selectively construct the (E)-1-methylpropenyl and (1E,2E)-4-carboxy-1,3-butadienyl substituents.

Original languageEnglish
Pages (from-to)553-556
Number of pages4
JournalOrganic Letters
Volume6
Issue number4
DOIs
Publication statusPublished - 2004 Feb 19

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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