Enantiospecific synthesis of (1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid by a modified Corey-Link reaction

Autor:	Modesta Espada, Carmen Pedregal, Carmen Dominguez, Stéphane Borrelly, Jesús Ezquerra, S. Richard Baker, Lourdes Prieto
Rok vydání:	1998
Předmět:	chemistry.chemical_classification Cyclopentenone Ketone Chloroform Organic Chemistry Diol Alcohol Biochemistry chemistry.chemical_compound Dicarboxylic acid chemistry Drug Discovery Sodium azide Organic chemistry Azide
Zdroj:	Tetrahedron Letters. 39:9305-9308
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(98)02092-9
Popis:	( 1S,2S,5R,6S )-2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740) was synthesised enantiospecifically from a sugar derived enantiomerically pure cyclopentenone. The α-amino acid stereogenic centre was formed by reacting the ketone with chloroform anion and then the alcohol so formed was reacted with sodium azide/DBU in methanol to give an azido ester. Critically, this modified Corey-Link reaction gives the opposite stereochemical outcome to the traditional Bucherer-Bergs and Strecker reactions. The azide was reduced and acylated, the 1,2 diol deoxygenated and the protecting groups removed to give LY354740 with an e.e.>98%.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::1a80598d4befde89459f626d06951fed https://doi.org/10.1016/s0040-4039(98)02092-9 Zobrazit plný text záznamu Full Text from ScienceDirect