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A new synthesis of alkaloid ( S )‐3‐hydroxypiperidin‐2‐one and its O ‐TBS protected derivative
Author(s) -
Huang PeiQiang,
Chen Guo,
Zheng Xiao
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440239
Subject(s) - chemistry , alkaloid , derivative (finance) , lactone , stereochemistry , borane , block (permutation group theory) , organic chemistry , catalysis , mathematics , financial economics , economics , geometry
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.