Issue 5, 2012

An efficient approach to dispacamide A and its derivatives

Abstract

Dispacamide A and new analogs of this marine alkaloid were prepared in seven steps with an overall yield ranging from 12 to 33%. The key step of the strategy was a stereocontrolled Knoevenagel condensation under microwave dielectric heating in the last step. In this condensation, the 2-aminoimidazolin-4-one hydrochloride partners 10a–c were synthesized in three steps with good overall yields (33–79%) via the ring closure of N-guanidino acetic acids 9a–c and the aldehydes 5a,b as the two others building-blocks, in 3 steps with 60–66% overall yields. The six synthetic products have been obtained with a Z geometry about their exocyclic bond on the basis of 13C/1H long-range coupling constants using a gHSQMBC experiment.

Graphical abstract: An efficient approach to dispacamide A and its derivatives

Supplementary files

Article information

Article type
Paper
Submitted
17 Aug 2011
Accepted
06 Oct 2011
First published
06 Oct 2011

Org. Biomol. Chem., 2012,10, 978-987

An efficient approach to dispacamide A and its derivatives

S. Guihéneuf, L. Paquin, F. Carreaux, E. Durieu, L. Meijer and J. P. Bazureau, Org. Biomol. Chem., 2012, 10, 978 DOI: 10.1039/C1OB06161E

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