期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 10, 期 5, 页码 978-987出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob06161e
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资金
- Ministere de la Recherche et de l'Enseignement Superieur
- French National Cancer Institute [PRIR 04-8390, ACI 04-2254]
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 C-13/H-1 long-range coupling constants using a gHSQMBC experiment.
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