Enantioselective aldol cyclodehydrations catalyzed by antibody 38C2

被引:68
作者
List, B
Lerner, RA
Barbas, CF
机构
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
关键词
D O I
10.1021/ol9905405
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aldolase antibody 38C2 catalyzes the enantioselective aldol cyclodehydration of 4-substituted-2,6-heptanediones (3) to give enantiomerically enriched 5-substituted-3-methyl-2-cyclohexen-1-ones (4). Yields, enantioselectivities, and product purities are markedly increased compared to the L-proline-catalyzed reactions.
引用
收藏
页码:59 / 61
页数:3
相关论文
共 24 条
[1]  
AGAMI C, 1987, B SOC CHIM FR, P358
[2]   Immune versus natural selection: Antibody aldolases with enzymic rates but broader scope [J].
Barbas, CF ;
Heine, A ;
Zhong, GF ;
Hoffmann, T ;
Gramatikova, S ;
Bjornestedt, R ;
List, B ;
Anderson, J ;
Stura, EA ;
Wilson, IA ;
Lerner, RA .
SCIENCE, 1997, 278 (5346) :2085-2092
[3]   TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES [J].
EDER, U ;
SAUER, G ;
WEICHERT, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) :496-&
[4]   ASYMMETRIC SYNTHESIS OF BICYCLIC INTERMEDIATES OF NATURAL PRODUCT CHEMISTRY [J].
HAJOS, ZG ;
PARRISH, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) :1615-1621
[5]   Aldolase antibodies of remarkable scope [J].
Hoffmann, T ;
Zhong, GF ;
List, B ;
Shabat, D ;
Anderson, J ;
Gramatikova, S ;
Lerner, RA ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (12) :2768-2779
[6]   LATENT ACETONYLATION OF ALPHA,BETA-ENONES WITH ALLYLTRIMETHYLSILANE OR 2-METHYL-2-PROPENYLTRIMETHYLSILANE - SYNTHESIS OF 1,5-DIKETONES AND ANNELATION TO FUSED CYCLOHEXENONES [J].
HOSOMI, A ;
KOBAYASHI, H ;
SAKURAI, H .
TETRAHEDRON LETTERS, 1980, 21 (10) :955-958
[7]   CHEMISTRY OF ORGANOSILICON COMPOUNDS .99. CONJUGATE ADDITION OF ALLYLSILANES TO ALPHA, BETA-ENONES - NEW METHOD OF STEREOSELECTIVE INTRODUCTION OF ANGULAR ALLYL GROUP IN FUSED CYCLIC ALPHA, BETA-ENONES [J].
HOSOMI, A ;
SAKURAI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (05) :1673-1675
[8]   CONTROLLING CHEMICAL-REACTIVITY WITH ANTIBODIES [J].
HSIEH, LC ;
YONKOVICH, S ;
KOCHERSPERGER, L ;
SCHULTZ, PG .
SCIENCE, 1993, 260 (5106) :337-339
[9]   ASYMMETRIC INDUCTION VIA A CATALYTIC ANTIBODY [J].
IKEDA, S ;
WEINHOUSE, MI ;
JANDA, KD ;
LERNER, RA ;
DANISHEFSKY, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7763-7764
[10]   ANTIBODY CATALYSIS OF A DISFAVORED CHEMICAL TRANSFORMATION [J].
JANDA, KD ;
SHEVLIN, CG ;
LERNER, RA .
SCIENCE, 1993, 259 (5094) :490-493