Issue 94, 2013
From the journal:

Chemical Communications

Stereoselective synthesis of (−)-lepadins A–C†

Mercedes Amat,*a   Alexandre Pinto,a   Rosa Grieraa  and  Joan Boscha  

* Corresponding authors

a Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona, 08028-Barcelona, Spain
E-mail: amat@ub.edu
Fax: +34 93 402 45 39
Tel: +34 93 402 45 40

Abstract

A concise synthesis of the marine alkaloids (−)-lepadins A–C from a phenylglycinol-derived tricyclic lactam is reported. Key steps from the stereochemical standpoint involve stereoselective cyclocondensation, double bond hydrogenation, oxazolidine opening, hydroboration–oxidation, and Horner–Wadsworth–Emmons reactions.

Graphical abstract: Stereoselective synthesis of (−)-lepadins A–C

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Article information

DOI
https://doi.org/10.1039/C3CC46801A
Article type
Communication
Submitted
05 Sep 2013
Accepted
05 Oct 2013
First published
07 Oct 2013

Chem. Commun., 2013,49, 11032-11034

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Stereoselective synthesis of (−)-lepadins A–C

M. Amat, A. Pinto, R. Griera and J. Bosch, Chem. Commun., 2013, 49, 11032 DOI: 10.1039/C3CC46801A

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