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 language | English |
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Pages (from-to) | 3963-3970 |
Number of pages | 8 |
Journal | European Journal of Organic Chemistry |
Volume | 2015 |
Issue number | 18 |
DOIs | |
Publication status | Published - 2015 Jun 1 |
Keywords
- Asymmetric synthesis
- Natural products
- Nitrogen heterocycles
- Synthetic methods
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry