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

3 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

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Stereoselectivity
Amides
Functional groups
synthesis
amides
reactivity
alkoxyl radical
fasicularin

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Asymmetric Total Synthesis of Fasicularin by Chiral N-Alkoxyamide Strategy. / Yamamoto, Shio; Komiya, Yukinori; Kobayashi, Akihiro; Minamikawa, Ryo; Oishi, Takeshi; Satou, Takaaki; Chida, Noritaka.

In: Organic Letters, Vol. 21, No. 6, 15.03.2019, p. 1868-1871.

Research output: Contribution to journalArticle

Yamamoto, Shio ; Komiya, Yukinori ; Kobayashi, Akihiro ; Minamikawa, Ryo ; Oishi, Takeshi ; Satou, Takaaki ; Chida, Noritaka. / Asymmetric Total Synthesis of Fasicularin by Chiral N-Alkoxyamide Strategy. In: Organic Letters. 2019 ; Vol. 21, No. 6. pp. 1868-1871.
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