Synthetic studies on (+)-bucidarasin C: Two diastereoselective transannular reactions producing cis-decaline derivatives that show reversal selectivity

Akinobu Nakahara, Misaki Kanbe, Masahisa Nakada

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

This manuscript describes studies on the construction of the cis-decaline core of (+)-bucidarasin C. The transannular Diels-Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis-decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis-decaline derivative as the major product.

Original languageEnglish
Pages (from-to)1518-1522
Number of pages5
JournalTetrahedron Letters
Volume53
Issue number12
DOIs
Publication statusPublished - 2012 Mar 21

Keywords

  • Bucidarasin
  • Cascade reaction
  • Diels-Alder reaction
  • Michael reaction
  • Stereoselective reaction
  • Transannular reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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