A Concise and Efficient Total Synthesis of Militarinone D

Uttam Dash, Sandip Sengupta, Taebo Sim

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

A highly stereoselective, concise (14 steps longest linear sequence and 20 steps overall), and efficient (15 % overall yield) synthesis of militarinone D has been accomplished. The key reactions utilized in the sequence are enzymatic desymmetrization, cis/trans isomerization, Horner–Wadsworth–Emmons olefination, and addition of an organolithium species to a highly conjugated chiral aldehyde. The simplicity of the strategy may enable its utilization in the large‐scale production of this target. Moreover, the strategy utilized to design the route should be applicable to the preparation of analogs that bear a variety of substituted pyridinone core structures.

Original languageEnglish
Pages (from-to)3963-3970
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number18
DOIs
Publication statusPublished - 2015 Jun

Keywords

  • Asymmetric synthesis
  • Natural products
  • Nitrogen heterocycles
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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