Enantioselective Total Synthesis of (-)-Misramine

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

Research output: Contribution to journalArticle

2 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 languageEnglish
Pages (from-to)5044-5047
Number of pages4
JournalOrganic Letters
Volume20
Issue number16
DOIs
Publication statusPublished - 2018 Aug 17

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Enantioselective Total Synthesis of (-)-Misramine'. Together they form a unique fingerprint.

  • 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