Synthetic studies on (+)-ophiobolin A: Asymmetric synthesis of the spirocyclic CD-ring moiety

Naoyoshi Noguchi, Masahisa Nakada

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Abstract

Asymmetric synthesis of the spirocyclic CD-ring moiety of (+)-ophiobolin A is described. Fragment A, which was prepared via pig liver esterase (PLE)-mediated kinetic resolution, and fragment B, which was prepared via diastereoselective allylation and subsequent kinetic iodolactonization, were coupled to afford the allylsilane 2, which was successfully cyclized to the desired spirocyclic CD-ring moiety 1a in the presence of a Lewis acid.

Original languageEnglish
Pages (from-to)2039-2042
Number of pages4
JournalOrganic Letters
Volume8
Issue number10
DOIs
Publication statusPublished - 2006 May 11

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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