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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 methods; Asymmetric synthesis; Natural products; Nitrogen heterocycles; ASYMMETRIC-SYNTHESIS; PYRIDONE ALKALOIDS; METABOLITES; TENELLIN
- 제목
- A Concise and Efficient Total Synthesis of Militarinone D
- 저자
- Dash, Uttam; Sengupta, Sandip; Sim, Taebo
- 발행일
- 2015-06
- 유형
- Article
- 권
- 2015
- 호
- 18
- 페이지
- 3963 ~ 3970