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Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2012

An efficient approach to dispacamide A and its derivatives.

Résumé

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 (13)C/(1)H long-range coupling constants using a gHSQMBC experiment.

Domaines

Chimie organique
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Dates et versions

hal-00870469 , version 1 (07-10-2013)

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Citer

Solène Guihéneuf, Ludovic Paquin, François Carreaux, Emilie Durieu, Laurent Meijer, et al.. An efficient approach to dispacamide A and its derivatives.. Organic & Biomolecular Chemistry, 2012, 10 (5), pp.978-87. ⟨10.1039/c1ob06161e⟩. ⟨hal-00870469⟩
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