Issue 14, 2004
From the journal:

Chemical Communications

Enantioselective formal synthesis of uleine alkaloids from phenylglycinol-derived bicyclic lactams†

Mercedes Amat,*a   Maria Pérez,a   Núria Llor,a   Marisa Martinelli,a   Elies Molinsb  and  Joan Bosch*a  

* Corresponding authors

a Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain
E-mail: amat@ub.edu, joanbosch@ub.edu
Fax: 34 93 4024539
Tel: 34 93 4024538

b Institut de Ciència de Materials (CSIC), Campus UAB, 08193-Cerdanyola, Spain

Abstract

A two-step route for the enantioselective construction of the tetracyclic ring system of uleine alkaloids, involving the stereoselective conjugate addition of an appropriate indole-containing nucleophile to a chiral bicyclic δ-lactam and the subsequent cyclization on the indole 3-position of the resulting 4,5-disubstituted 2-piperidone, has culminated in the formal total synthesis of several alkaloids of this group.

Graphical abstract: Enantioselective formal synthesis of uleine alkaloids from phenylglycinol-derived bicyclic lactams

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Article information

DOI
https://doi.org/10.1039/B400987H
Article type
Communication
Submitted
21 Jan 2004
Accepted
11 May 2004
First published
14 Jun 2004

Chem. Commun., 2004, 1602-1603

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Enantioselective formal synthesis of uleine alkaloids from phenylglycinol-derived bicyclic lactams

M. Amat, M. Pérez, N. Llor, M. Martinelli, E. Molins and J. Bosch, Chem. Commun., 2004, 1602 DOI: 10.1039/B400987H

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