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Total Synthesis of (+)-Kalmanol.

作者信息

Ma Tianhao, Ma Yiming, Li Bo, Jia Yanxing

机构信息

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, and Chemical Biology Center, Peking University, Xue Yuan Rd. 38, Beijing, 100191, China.

出版信息

Angew Chem Int Ed Engl. 2024 Oct 14;63(42):e202407215. doi: 10.1002/anie.202407215. Epub 2024 Sep 13.

DOI:10.1002/anie.202407215
PMID:39082673
Abstract

Kalmanol, the flagship member of the kalmane diterpene family, possesses a complex and highly oxidized 5/5/8/5 tetracyclic skeleton with nine contiguous stereocenters and exhibits significant analgesic effects and cardiotoxic properties. We have achieved the efficient total synthesis of (+)-kalmanol in 22 steps with 2.3 % yield. The synthesis featured a Rh-catalyzed [5+2+1] cycloaddition reaction to construct 5/5/8 tricyclic skeleton, and a meticulously designed sequence of stereoselective oxidations of the 5/5/8/5 tetracyclic skeleton.

摘要

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