Asymmetric synthesis of (S)-(-)-acromelobinic acid

被引:8
作者
Adamczyk, M [1 ]
Akireddy, SR [1 ]
Reddy, RE [1 ]
机构
[1] Abbott Labs, Dept Chem, Div Diagnost, Abbott Pk, IL 60064 USA
关键词
D O I
10.1016/S0957-4166(01)00414-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A total synthesis of (S)-(-)-acromelobinic acid 2, which was isolated from elitocybe acromelalga, was achieved via an asymmetric hydrogenation protocol. Dehydroamino acid derivative 12 was prepared from 2.5-lutidine 5 and subjected to asymmetric hydrogenation using (S,S)-[Rh(Et-DuPHOS)(COD)]BF4 to give the (S)-(+)-pyridylalanine derivative 13 in 93% yield and > 96% e.e. Removal of the protecting groups in (S)-(+)-13 afforded (S)-(-)-acromelobinic acid 2. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2385 / 2387
页数:3
相关论文
共 21 条
[1]   An efficient enantioselective synthesis of (S)-(-)-acromelobic acid [J].
Adamczyk, M ;
Akireddy, SR ;
Reddy, RE .
ORGANIC LETTERS, 2000, 2 (22) :3421-3423
[2]  
Adamczyk M, 1999, ANGEW CHEM INT EDIT, V38, P3537, DOI 10.1002/(SICI)1521-3773(19991203)38:23<3537::AID-ANIE3537>3.3.CO
[3]  
2-I
[4]   A concise synthesis of (S)-(-)-3-(2-carboxy-4-pyrrolyl)-alanine [J].
Adamczyk, M ;
Johnson, DD ;
Reddy, RE .
TETRAHEDRON-ASYMMETRY, 2000, 11 (15) :3063-3068
[5]   Bone collagen cross-links: an efficient one-pot synthesis of (+)-pyridinoline and (+)-deoxypyridinoline [J].
Adamczyk, M ;
Johnson, DD ;
Reddy, RE .
TETRAHEDRON-ASYMMETRY, 2000, 11 (11) :2289-2298
[6]   Collagen cross-links: Synthesis of pyridinoline, deoxypyridinoline and their analogues [J].
Adamczyk, M ;
Johnson, DD ;
Reddy, RE .
TETRAHEDRON, 1999, 55 (01) :63-88
[7]   Versatile synthesis of (+)-deoxypyridinoline, a biochemical marker for diagnosis of osteoporosis [J].
Adamczyk, M ;
Akireddy, SR ;
Reddy, RE .
TETRAHEDRON-ASYMMETRY, 1999, 10 (16) :3107-3110
[8]  
ANGYAL SJ, 1954, ORG REACTIONS, V8, P197
[9]   PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ ;
FEASTER, JE ;
NUGENT, WA ;
HARLOW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138
[10]  
BUYUK G, 1975, HELV CHIM ACTA, V58, P78