A new synthesis of hydroxyethylene dipeptide isosteres for Leu-Leu and Phe-Phe in their y-lactone form la and lb employing β-amino-a-hydroxy aldehydes with singly and doubly protected nitrogen has been developed. These key intermediates, which are available through the thiazole—aldehyde synthesis from L-leucine and L-phenylalanine, weee converted to alkanoates by Wittig olefination and reduction of the ethylenic double bond. Lactonization and stereoselective alkylation at C-2 of the resulting lactones completed the building up of the structural framework. Overall yields weee in the range 16—19% for la and 22—23% for lb. © 1995, American Chemical Society. All rights reserved.
THIAZOLE-BASED STEREOSELECTIVE ROUTES TO LEUCINE AND PHENYLALANINE HYDROXYETHYLENE DIPEPTIDE ISOSTERE INHIBITORS OF RENIN AND HIV-1 ASPARTIC PROTEASE
DONDONI, Alessandro;PERRONE, Daniela;
1995
Abstract
A new synthesis of hydroxyethylene dipeptide isosteres for Leu-Leu and Phe-Phe in their y-lactone form la and lb employing β-amino-a-hydroxy aldehydes with singly and doubly protected nitrogen has been developed. These key intermediates, which are available through the thiazole—aldehyde synthesis from L-leucine and L-phenylalanine, weee converted to alkanoates by Wittig olefination and reduction of the ethylenic double bond. Lactonization and stereoselective alkylation at C-2 of the resulting lactones completed the building up of the structural framework. Overall yields weee in the range 16—19% for la and 22—23% for lb. © 1995, American Chemical Society. All rights reserved.I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
