Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 11, Issue -, Pages 1060-1067Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.11.119
Keywords
Aube reaction; biological activity; carbocyclic nucleosides; cyclopentenylated lactams; cyclopentylated lactams
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Funding
- CSIR, New Delhi through CSIR-NCL Joint Collaborative Program [BSC0124]
- CSIR, New Delhi
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A novel and convenient method utilizing the Aube reaction to access a new class of compounds that are similar to carbocyclic nucleosides is reported. The azido alcohol derived from Vince lactam undergoes the Aube reaction with various cyclic ketones to give cyclopentenyl-substituted lactams. Upon dihydroxylation, this affords the N-cyclopentenyl-lactam compounds in racemic form. Given the numerous uses of nucleosides and related compounds, we were interested in the synthesis of carbocylic nucleoside mimics. The attempts and results are described herein.
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