Studies on the diastereoselectivity in the IMDA reactions of terminally activated (E,E,E)-nona-1,6,8-trienes

Takahiro Suzuki, Natsumi Tanaka, Takehiko Matsumura, Yosuke Hosoya, Masahisa Nakada

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The structure-diastereoselectivity relationships in the IMDA reactions of the terminally activated (E,E,E)-nona-1,6,8-trienes have been studied. It is found that the configuration of the C3 position bearing the protected hydroxyl group is crucial to the diastereoselectivity, and the magnitude of the ratio depends on the relative configuration of the C3-C5 positions. The results obtained in this study including the new successful IMDA reactions would be useful for the stereoselective synthesis of natural products containing a bicyclo[4.3.0]non-2-ene carbon skeleton.

Original languageEnglish
Pages (from-to)1593-1598
Number of pages6
JournalTetrahedron Letters
Volume47
Issue number10
DOIs
Publication statusPublished - 2006 Mar 6

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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