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Updated: Feb 7, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
Published on: January 17, 2020
Enantioselective Total Synthesis of (-)-Misramine
Keisuke Yoshida1, Yuta Fujino2, Yusei Takamatsu2
1Faculty of Pharmacy , Meijo University , 150 Yagotoyama , Tempaku-ku , Nagoya 468-8503 , Japan.
Abstract:
The enantioselective total synthesis of an unusual pentacyclic proaporphine alkaloid, (-)-misramine, was achieved. The synthetic strategy relied on an enantioselective intramolecular Friedel-Crafts-type 1,4-addition using an asymmetric organocatalyst to construct a spiroindane skeleton containing an all-carbon quaternary stereocenter and a double reductive amination of the keto-aldehyde to form a piperidine ring toward the end of the synthesis. This work is the first example of asymmetric synthesis of a proaporphine alkaloid.
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