Asymmetric Total Synthesis of Fasicularin by Chiral N‑Alkoxyamide Strategy

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 a...

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Bibliographic Details
Published in:Organic letters 2019-03, Vol.21 (6), p.1868-1871
Main Authors: Yamamoto, Shio, Komiya, Yukinori, Kobayashi, Akihiro, Minamikawa, Ryo, Oishi, Takeshi, Sato, Takaaki, Chida, Noritaka
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00478