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Shinde MV, Ople RS, Sangtani E, et al. Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction. Beilstein J Org Chem. 2015;11:1060-7doi: 10.3762/bjoc.11.119.
Shinde, M. V., Ople, R. S., Sangtani, E., Gonnade, R., & Reddy, D. S. (2015). Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction. Beilstein journal of organic chemistry, 111060-7. https://doi.org/10.3762/bjoc.11.119
Shinde, Madhuri V, et al. "Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction." Beilstein journal of organic chemistry vol. 11 (2015): 1060-7. doi: https://doi.org/10.3762/bjoc.11.119
Shinde MV, Ople RS, Sangtani E, Gonnade R, Reddy DS. Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction. Beilstein J Org Chem. 2015 Jun 23;11:1060-7. doi: 10.3762/bjoc.11.119. eCollection 2015. PMID: 26199661; PMCID: PMC4505090.
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Beilstein J Org Chem. 2015 Jun 23;11:1060-7. doi: 10.3762/bjoc.11.119. eCollection 2015.

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

Beilstein journal of organic chemistry

Madhuri V Shinde, Rohini S Ople, Ekta Sangtani, Rajesh Gonnade, D Srinivasa Reddy

Affiliations

  1. Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India.
  2. Center for Material Characterization, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India.

PMID: 26199661 PMCID: PMC4505090 DOI: 10.3762/bjoc.11.119

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.

Keywords: Aubé reaction; biological activity; carbocyclic nucleosides; cyclopentenylated lactams; cyclopentylated lactams

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