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

被引：21

作者：

Adamczyk, M ^{[1
]}

Akireddy, SR ^{[1
]}

Reddy, RE ^{[1
]}

机构：

[1] Abbott Labs, Div Diagnost, Dept Chem, Abbott Pk, IL 60064 USA

来源：

TETRAHEDRON | 2002年 / 58卷 / 34期

关键词：

nonproteinogenic amino acids; total synthesis; acromelobic acid; acromelobinic acid;

D O I：

10.1016/S0040-4020(02)00670-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 33 required for the synthesis of (S)-(-)-2 was prepared from 2,5-lutidine (27), which upon hydrogenation using (S,S)-[Rh(Et-DuPHOS)(COD)]BF4 catalyst afforded (S)-(+)-34 in 93% yield and >96% ee. Removal of protective groups in (S)-(+)-34 afforded (S)-(-)-acromelobinic acid (2) in good overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：6951 / 6963

页数：13

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