A Concise and Efficient Total Synthesis of Militarinone D

  • Dash, Uttam
  • Sengupta, Sandip
  • Sim, Taebo
Citations

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초록

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.

키워드

Synthetic methodsAsymmetric synthesisNatural productsNitrogen heterocyclesASYMMETRIC-SYNTHESISPYRIDONE ALKALOIDSMETABOLITESTENELLIN
제목
A Concise and Efficient Total Synthesis of Militarinone D
저자
Dash, UttamSengupta, SandipSim, Taebo
DOI
10.1002/ejoc.201500380
발행일
2015-06
유형
Article
저널명
European Journal of Organic Chemistry
2015
18
페이지
3963 ~ 3970