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Synthesis of novel N-cyclopentenyl-lactams using the Aube reaction.

ABSTRACT: A novel and convenient method utilizing the Aubé 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 Aubé 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.

SUBMITTER: Shinde MV

PROVIDER: S-EPMC4505090 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction.

Shinde Madhuri V MV Ople Rohini S RS Sangtani Ekta E Gonnade Rajesh R Reddy D Srinivasa DS

Beilstein journal of organic chemistry 20150623

A novel and convenient method utilizing the Aubé 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 Aubé 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 nucleo ...[more]

PMID: 26199661

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