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 journalArticlepeer-review

11 Citations (Scopus)


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
Issue number16
Publication statusPublished - 2018 Aug 17

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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