Enantioselective Approach to (∿-Hamigeran B and (∿-4-Bromohamigeran B via Catalytic Asymmetric Hydrogenation of Racemic Ketone To Assemble the Chiral Core Framework

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• 作者：Han Lin ; Li-Jun Xiao ; Min-Jie Zhou ; Hong-Ming Yu ; Jian-Hua Xie ; Qi-Lin Zhou
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：March 18, 2016
• 年：2016
• 卷：18
• 期：6
• 页码：1434-1437
• 全文大小：417K
• ISSN：1523-7052

文摘

A new strategy featuring an iridium-catalyzed asymmetric hydrogenation of a racemic ketone via dynamic kinetic resolution to generate a cyclopentanol with three contiguous stereocenters and a SmI₂-promoted pinacol coupling to install the six-membered ring with correct stereochemistry has been described for the enantioselective total synthesis of (−)-hamigeran B (19 steps, 10.6% overall yield) and (−)-4-bromohamigeran B (19 steps, 12.3% overall yield).