Synthesis of (+)-madindoline A and (+)-madindoline B

  • Org Lett. 2007 Feb 15;9(4):647-50. doi: 10.1021/ol062919e.
Lifeng Wan  1 ,  Marcus A Tius
Affiliations
  • 1. Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, Hawaii 96822, USA.
PMID: 17286372 DOI: 10.1021/ol062919e
Abstract

The allene ether version of the Nazarov cyclization was used to construct the cyclopentane dione portion of madindolines A and B. The racemic cyclopentane dione from the Nazarov cyclization was converted to an enol ether that was combined with the chiral, nonracemic hydroxyfuroindoline in a Mannich reaction. Deprotection and oxidation led to (+)-madindoline A and (+)-madindoline B. [reaction: see text].

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