Total synthesis of a novel macrotetrolide

Ludovic Coutable, Karim Adil, Christine Saluzzo*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

The total synthesis of a novel macrotetrolide, an isobutyl nonactin analog, has been achieved in 15% yield by coupling both enantiomers of the corresponding nonactic acid analogs followed by macrolactonization. These building blocks were prepared starting from β-ketoester in nine steps and 34% overall yield, in an efficient and highly stereoselective sequence. The key steps of the strategy are asymmetric hydrogenation, chelation-controlled allylation, intramolecular haloetherification of bishomoallylic ether presenting a trisubstituted double bond deactivated by an ester, and finally a stereoselective reduction of α-bromoester.

Original languageEnglish (US)
Pages (from-to)11296-11303
Number of pages8
JournalTetrahedron
Volume64
Issue number49
DOIs
StatePublished - Dec 1 2008

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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