Issue 11, 2013
From the journal:

Organic & Biomolecular Chemistry

Synthesis of highly functionalized pyrrolidines as tunable templates for the direct access to (±)-coerulescine and the tricyclic core of martinellines

Ronan Le Goff,a   Ata Martin Lawson,a   Adam Daïcha  and  Sébastien Comesse*a  

* Corresponding authors

a URCOM, EA 3221, INC3M, FR-CNRS 3038, UFR des Sciences & Techniques de l'Université du Havre, BP: 540, 25 rue Philippe Lebon, F-76058 Le Havre Cedex, France
E-mail: sebastien.comesse@univ-lehavre.fr
Fax: +033 (0)2 32 74 43 91
Tel: +033 (0)2 32 74 44 03

Abstract

An aza-Michael induced ring closure (aza-MIRC) tandem reaction of benzyl (2-bromoethyl)carbamate with various Michael acceptors is described. The N-Cbz-β-gem-disubstituted pyrrolidines thus obtained were proved to be versatile intermediates for the rapid access to both martinelline and spirooxindole backbones. An application of this strategy towards an expedient 4 step total synthesis of (±)-coerulescine is also presented.

Graphical abstract: Synthesis of highly functionalized pyrrolidines as tunable templates for the direct access to (±)-coerulescine and the tricyclic core of martinellines

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Article information

DOI
https://doi.org/10.1039/C3OB27472A
Article type
Communication
Submitted
20 Dec 2012
Accepted
25 Jan 2013
First published
28 Jan 2013

Org. Biomol. Chem., 2013,11, 1818-1821

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Synthesis of highly functionalized pyrrolidines as tunable templates for the direct access to (±)-coerulescine and the tricyclic core of martinellines

R. Le Goff, A. M. Lawson, A. Daïch and S. Comesse, Org. Biomol. Chem., 2013, 11, 1818 DOI: 10.1039/C3OB27472A

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