Aldol reactions of ketal-protected tartrate ester enolates. Asymmetric syntheses and absolute stereochemical assignments of phospholipase A2 inhibitors cinatrin C1 and C3

David A. Evans, B. Wesley Trotter, James C. Barrow

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient approach to the syntheses of cinatrins C1 and C3 has been developed and used to establish the absolute configurations of these natural products. The construction of each molecule has been achieved in a five-step reaction sequence (overall yield 43% for cinatrin C1, 33% for cinatrin C3) from the di-tert-butyl ester of (R,R)-tartaric acid. The two contiguous, quaternary chiral centers in the cinatrin skeleton are constructed via a diastereoselective, titanium-mediated aldol coupling of a tartrate-derived silylketene acetal and an achiral α-ketoester. This bond construction proceeds with excellent diastereoselectivity for a variety of aldehyde and α-ketoester substrates.

Original languageEnglish (US)
Pages (from-to)8779-8794
Number of pages16
JournalTetrahedron
Volume53
Issue number26
DOIs
StatePublished - Jun 30 1997
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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