Iterative direct aldol strategy for polypropionates: Enantioselective total synthesis of (-)-membrenone a and B

Kaliyamoorthy Alagiri, Shaoquan Lin, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

An iterative direct aldol reaction using a C3 propionate unit as an aldol donor offers expeditious access to polyketide assembly in a highly diastereo- and enantioselective manner. An all-syn polyketide array with four consecutive stereogenic centers was efficiently constructed by an aldol reaction of thiopropionamide via soft Lewis acid/hard Brønsted base cooperative catalysis. This iterative aldol strategy led to an enantioselective synthesis of (-)-membrenone A and B. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)5301-5303
Number of pages3
JournalOrganic Letters
Volume16
Issue number20
DOIs
Publication statusPublished - 2014 Oct 17
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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