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 › peer-review

3 Citations (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

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Enantioselective Total Synthesis of (-)-Misramine",

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.",

author = "Keisuke Yoshida and Yuta Fujino and Yusei Takamatsu and Kohei Matsui and Akihiro Ogura and Yuri Fukami and Shinji Kitagaki and Takao, {Ken Ichi}",

note = "Funding Information: This research was supported by JSPS KAKENHI Grant Number 16K17903.",

year = "2018",

month = aug,

day = "17",

doi = "10.1021/acs.orglett.8b02198",

language = "English",

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T1 - Enantioselective Total Synthesis of (-)-Misramine

AU - Yoshida, Keisuke

AU - Fujino, Yuta

AU - Takamatsu, Yusei

AU - Matsui, Kohei

AU - Ogura, Akihiro

AU - Fukami, Yuri

AU - Kitagaki, Shinji

AU - Takao, Ken Ichi

N1 - Funding Information: This research was supported by JSPS KAKENHI Grant Number 16K17903.

PY - 2018/8/17

Y1 - 2018/8/17

N2 - 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.

AB - 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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