Asymmetric Total Synthesis of Fasicularin by Chiral N-Alkoxyamide Strategy

Shio Yamamoto; Yukinori Komiya; Akihiro Kobayashi; Ryo Minamikawa; Takeshi Oishi; Takaaki Sato; Noritaka Chida

doi:10.1021/acs.orglett.9b00478

Asymmetric Total Synthesis of Fasicularin by Chiral N-Alkoxyamide Strategy

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

Research output: Contribution to journal › Article › peer-review

21 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 language	English
Pages (from-to)	1868-1871
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.9b00478
Publication status	Published - 2019 Mar 15

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b00478

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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.",

author = "Shio Yamamoto and Yukinori Komiya and Akihiro Kobayashi and Ryo Minamikawa and Takeshi Oishi and Takaaki Sato and Noritaka Chida",

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T1 - Asymmetric Total Synthesis of Fasicularin by Chiral N-Alkoxyamide Strategy

AU - Yamamoto, Shio

AU - Komiya, Yukinori

AU - Kobayashi, Akihiro

AU - Minamikawa, Ryo

AU - Oishi, Takeshi

AU - Sato, Takaaki

AU - Chida, Noritaka

N1 - Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (C) from MEXT (15K05436), the Tobe Maki Foundation, and the JGC-S Scholarship Foundation. Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/3/15

Y1 - 2019/3/15

N2 - 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.

AB - 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.

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Asymmetric Total Synthesis of Fasicularin by Chiral N-Alkoxyamide Strategy

Abstract

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