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

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

Research output: Contribution to journalArticle

18 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

Fingerprint

Cyclobutanes
Heptanes
Lewis Acids
Acetals
Cycloaddition Reaction
Carbon
Derivatives
Cycloaddition
Protonation
Hydrides
camphorsultam
pestalotiopsin A

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthetic studies of pestalotiopsin A : Asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure. / Takao, Kenichi; Saegusa, Hiroshi; Tsujita, Tomohiro; Washizawa, Takenori; Tadano, Kin Ichi.

In: Tetrahedron Letters, Vol. 46, No. 35, 29.08.2005, p. 5815-5818.

Research output: Contribution to journalArticle

Takao, Kenichi ; Saegusa, Hiroshi ; Tsujita, Tomohiro ; Washizawa, Takenori ; Tadano, Kin Ichi. / Synthetic studies of pestalotiopsin A : Asymmetric synthesis of the 2-oxabicyclo[3.2.0]heptane substructure. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 35. pp. 5815-5818.
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