A Concise and Efficient Total Synthesis of Militarinone D

Uttam Dash, Sandip Sengupta, Taebo Sim

Research output: Contribution to journalArticle

5 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. A highly efficient (15 % overall yield) and convergent (longest linear sequence of 14 steps) synthesis of militarinone D from a known intermediate has been accomplished.

Original languageEnglish
Pages (from-to)3963-3970
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number18
DOIs
Publication statusPublished - 2015 Jun 1

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Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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