title: 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 (13)C/(1)H long-range coupling constants using a gHSQMBC experiment.
authors.affiliation: Université de Rennes 1, Laboratoire Sciences Chimiques de Rennes, UMR CNRS 6226, Groupe Ingénierie Chimique & Molécules pour le Vivant (ICMV), Campus de Beaulieu, Rennes, France.
authors.forename: Solène
authors.initials: S
authors.lastname: Guihéneuf
authors.forename: Ludovic
authors.initials: L
authors.lastname: Paquin
authors.forename: François
authors.initials: F
authors.lastname: Carreaux
authors.forename: Emilie
authors.initials: E
authors.lastname: Durieu
authors.forename: Laurent
authors.initials: L
authors.lastname: Meijer
authors.forename: Jean Pierre
authors.initials: JP
authors.lastname: Bazureau
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000191:economics / Q000379:methods; D006361:Heating; D008872:Microwaves; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001688:Biological Products