Model studies towards a biomimetic synthesis of keramaphidin B and halicyclamine A

Autor:	Bhupesh C. Das, Laurent Frédéric Gil, Xavier Baucherel, Marie-Thérèse Martin, Christian Marazano
Rok vydání:	1995
Předmět:	chemistry.chemical_classification Stereochemistry Organic Chemistry Salt (chemistry) Condensation reaction Biochemistry Adduct Sodium borohydride chemistry.chemical_compound chemistry Biosynthesis Biomimetic synthesis Drug Discovery Organic chemistry Triethylamine Dichloromethane
Zdroj:	Tetrahedron Letters. 36:6231-6234
ISSN:	0040-4039
DOI:	10.1016/0040-4039(95)01270-r
Popis:	As a model for condensation reactions of macrocycles of type 1 , which are possibly implicated in the biosynthesis of a number of new alkaloids recently extracted from sponges, we now report that treatment of dihydropyridinium salt 13 with triethylamine in dichloromethane gave, after reduction with sodium borohydride, adducts 15 and 16 in 25% and 7% isolated yields, respectively. The structures of these adducts are identical to the core structures of keramaphidin B, a biogenetic precursor of manzamines, and halicyclamine A.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::585720117b8aa87224de29b3c302e67e https://doi.org/10.1016/0040-4039(95)01270-r Zobrazit plný text záznamu Full Text from ScienceDirect