Advanced synthesis & catalysis

The Efficient and Enantiospecific Total Synthesis of Cyclopenta [b] phenanthrenes Structurally??Related to Neurosteroids

M Qian, DF Covey

文献索引：Qian, Mingxing; Covey, Douglas F. Advanced Synthesis and Catalysis, 2010 , vol. 352, # 11-12 p. 2057 - 2061

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被引用次数: 5

摘要

Abstract We report an efficient synthesis of cyclopenta [b] phenanthrenes functionalized at C- 3 and C-8 from an optically pure Hajos–Parrish ketone. The key step is a neutral alumina- catalyzed Michael addition of a Hajos–Parrish ketone derivative (4) to 1, 7-octadien-3-one (2) in 98% yield. This Michael addition product went through Krapcho decarbomethoxylation, aldol condensation, lithium liquid ammonia reduction, Wacker ...