Enantioselective Total Synthesis of (-)-Misramine

Keisuke Yoshida; Yuta Fujino; Yusei Takamatsu; Kohei Matsui; Akihiro Ogura; Yuri Fukami; Shinji Kitagaki; Ken-Ichi Takao

doi:10.1021/acs.orglett.8b02198

Enantioselective Total Synthesis of (-)-Misramine

Keisuke Yoshida, Yuta Fujino, Yusei Takamatsu, Kohei Matsui, Akihiro Ogura, Yuri Fukami, Shinji Kitagaki, Ken-Ichi Takao

Department of Applied Chemistry

Research output: Contribution to journal › Article

1 Citation (Scopus)

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.

Original language	English
Pages (from-to)	5044-5047
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.8b02198
Publication status	Published - 2018 Aug 17

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ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Yoshida, K., Fujino, Y., Takamatsu, Y., Matsui, K., Ogura, A., Fukami, Y., Kitagaki, S., & Takao, K-I. (2018). Enantioselective Total Synthesis of (-)-Misramine. Organic Letters, 20(16), 5044-5047. https://doi.org/10.1021/acs.orglett.8b02198

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AU - Fukami, Yuri

AU - Kitagaki, Shinji

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10.1021/acs.orglett.8b02198