Asymmetric Total Synthesis of Fasicularin by Chiral N-Alkoxyamide Strategy

Shio Yamamoto, Yukinori Komiya, Akihiro Kobayashi, Ryo Minamikawa, Takeshi Oishi, Takaaki Satou, Noritaka Chida

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The asymmetric total synthesis of fasicularin is reported. The key to success is the use of a chiral N-alkoxyamide to control both reactivity and stereoselectivity. This functional group enables the aza-spirocyclization and the reductive Strecker reaction, which cannot be realized with an ordinary amide. In addition, use of the chiral alkoxy group establishes two consecutive stereocenters in the aza-spirocyclization through remote stereocontrol.

Original languageEnglish
Pages (from-to)1868-1871
Number of pages4
JournalOrganic Letters
Volume21
Issue number6
DOIs
Publication statusPublished - 2019 Mar 15

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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