Issue 33, 2013
From the journal:

RSC Advances

Ti(iii)-mediated radical cyclization of epoxy-β-aminoacrylate in the synthesis of the substituted pyrrolidine core of necine bases: synthesis of 2-epi-rosmarinecine†

Sandip Basu,a   Pancham S. Kandiyal,b   Ravi Sankar Ampapathib  and  Tushar Kanti Chakraborty*a  

* Corresponding authors

a Department of Medicinal & Process Chemistry, Lucknow 226031, India
E-mail: chakraborty@cdri.res.in
Fax: +91-522-2771941
Tel: +91-522-2771940

b NMR Centre, SAIF Divison, CSIR-Central Drug Research Institute, Lucknow 226031, India

Abstract

A radical-mediated approach to the necine base 2-epi-rosmarinecine is described. The synthesis is based on the stereoselective formation of a highly substituted pyrrolidine ring from β-aminoacrylate, diastereoselective allylation and intramolecular cyclization.

Graphical abstract: Ti(iii)-mediated radical cyclization of epoxy-β-aminoacrylate in the synthesis of the substituted pyrrolidine core of necine bases: synthesis of 2-epi-rosmarinecine

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Article information

DOI
https://doi.org/10.1039/C3RA42315H
Article type
Communication
Submitted
10 May 2013
Accepted
24 Jun 2013
First published
25 Jun 2013

RSC Adv., 2013,3, 13630-13634

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Ti(III)-mediated radical cyclization of epoxy-β-aminoacrylate in the synthesis of the substituted pyrrolidine core of necine bases: synthesis of 2-epi-rosmarinecine

S. Basu, P. S. Kandiyal, R. S. Ampapathi and T. K. Chakraborty, RSC Adv., 2013, 3, 13630 DOI: 10.1039/C3RA42315H

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