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A new synthesis of alkaloid (S)-3-hydroxypiperidin-2-one and its O-TBS protected derivative

✍ Scribed by Pei-Qiang Huang; Guo Chen; Xiao Zheng

Publisher
Journal of Heterocyclic Chemistry
Year
2007
Tongue
English
Weight
253 KB
Volume
44
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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From the known lactone (S)‐4, easily derived from L‐glutamic acid, a scalable approach to chiral building block O‐silylated 3‐hydroxypiperidin‐2‐one 3 and alkaloid 1 was achieved in five and six‐steps respectively. The key steps are a chemoselective amidation of lactone‐ester 5 and a one‐pot reductive borane‐decomplexation, N‐debenzylation and cyclization.

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