Synthetic studies of pestalotiopsin A: Asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure

Ken Ichi Takao, Hiroshi Saegusa, Tomohiro Tsujita, Takenori Washizawa, Kin Ichi Tadano

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19 Citations (Scopus)

Abstract

A functionalized 2-oxabicyclo[3.2.0]heptan-3-one derivative, possessing all the skeletal carbons of pestalotiopsin A, has been synthesized. For the preparation of intermediary cyclobutane derivatives in enantioenriched form, the Lewis acid-catalyzed [2+2] cycloaddition of N-propiolated Oppolzer's camphorsultam with dimethylketene bis(trimethylsilyl) acetal followed by a stereoselective 1,4-hydride addition/protonation, has been developed.

Original languageEnglish
Pages (from-to)5815-5818
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number35
DOIs
Publication statusPublished - 2005 Aug 29

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Keywords

  • Chiral auxiliary
  • Cyclobutane
  • [2+2] Cycloaddition

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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