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- Title
Synthesis of 3,4-Fused γ-Lactone-γ-Lactam Bicyclic Moieties as Multifunctional Synthons for Bioactive Molecules.
- Authors
Shaameri, Zurina; Azib, Nur Aini; Mohamat, Mohd Fazli; Hamzah, Ahmad Sazali
- Abstract
A short approach for the synthesis of 3,4-fused γ-lactone-γ-lactam bicyclic systems ( 1) in diastereomeric mixtures from chiral D-alanine methyl ester hydrochloride is described. The key step towards is the reduction of the carbonyl ketone of the 5 R-configured 3,5-dimethylpyrrolidine-2,4-dione diastereomers ( 8) via sodium borohydride in the presence of . With the presence of ethyl acetyl functionality at C3-position, of 8 occurred concomitantly with keto reduction leading to and eventually affording the anticipated (3 S,4 S, 5R), (3 R,4 R, 5R), (3 R,4 S, 5R) and (3 S,4 R, 5R) bicyclic moieties. The formation of the fused systems was confirmed by mass spectroscopy (MS) and (NMR) analyses.
- Subjects
LACTAMS; CHEMICAL synthesis; BIOACTIVE compounds; MOIETIES (Chemistry); LACTONE derivatives; MASS spectrometry
- Publication
Journal of Heterocyclic Chemistry, 2016, Vol 53, Issue 4, p1059
- ISSN
0022-152X
- Publication type
Article
- DOI
10.1002/jhet.2433