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

Huang PeiQiang | Zendy; Chen Guo | Zendy; Zheng Xiao | Zendy

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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.

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