Tetrahedron

Nonproteinogenic amino acids: an efficient asymmetric synthesis of (S)-(−)-acromelobic acid and (S)-(−)-acromelobinic acid

M Adamczyk, SR Akireddy, RE Reddy

Index: Adamczyk, Maciej; Akireddy, Srinivasa Rao; Reddy, Rajarathnam E Tetrahedron, 2002 , vol. 58, # 34 p. 6951 - 6963

Full Text: HTML

Citation Number: 30

Abstract

An efficient synthesis of (S)-(−)-acromelobic acid (1) and (S)-(−)-acromelobinic acid (2) is described via asymmetric hydrogenation protocol. Asymmetric hydrogenation of dehydroamino acid derivative 23 using (R, R)-[Rh (DIPAMP)(COD)] BF4 catalyst followed by removal of the protective groups afforded (S)-(−)-acromelobic acid (1) in> 98% ee. The key intermediate 23 was prepared from citrazinic acid (8). The dehydroamino acid derivative ...