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

✍ Scribed by Mingxing Qian; Douglas F. Covey

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
180 KB
Volume
352
Category
Article
ISSN
1615-4150

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✦ Synopsis

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 oxidation and acid‐catalyzed cyclization to form cyclopenta[b]phenanthrene (1a) in 37% overall yield for the 7 steps.

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