Journal of the American Chemical Society

Enantioselective total synthesis of (-)-chlorothricolide

WR Roush, RJ Sciotti

文献索引：Roush, William R.; Sciotti, Richard J. Journal of the American Chemical Society, 1994 , vol. 116, # 14 p. 6457 - 6458

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被引用次数: 135

摘要

Hexaenoate 3 was synthesized by a 10-step sequence from the known acetylenic ketone 5.6 Thus, asymmetric reduction of 5 with the chiral borane generated in situ from (-)-a- pinene and 9-BBN (neat)'and protection of the resulting alcohol (89-94% ee) as a MOM ether provided 6 in 71% yield overall. a-Iodo vinylsilane 7 was prepared in 79% yield by a three-step sequence involving partial DIBAL reduction of the carbomethoxyl group, ...