ENZYMES IN ORGANIC-SYNTHESIS .20. SYNTHESIS OF (3R,5S)-3-HYDROXY-7-PHENYL-6-HEPTYN-5-OLIDE BY AN ENANTIOSELECTIVE ENZYME-CATALYZED LACTONIZATION OF A RACEMIC 3,5-DIHYDROXY ESTER

被引:12
作者
HENKEL, B [1 ]
KUNATH, A [1 ]
SCHICK, H [1 ]
机构
[1] CTR SELECT ORGAN SYNTH,D-12489 BERLIN,GERMANY
关键词
D O I
10.1016/S0957-4166(00)80473-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(3R,5S)-3-Hydroxy-7-phenyl-6-heptyn-5-olide was obtained with a high enantiomeric excess by an enzyme-catalyzed enantioselective lactonization of the corresponding methyl(3R*,5S*)-dihydroxyalkynoate followed by spontaneous crystallization.
引用
收藏
页码:17 / 18
页数:2
相关论文
共 8 条
[1]   A REMARKABLE SHORT SYNTHESIS OF OPTICALLY-ACTIVE MEVINIC ACID ANALOGS BY BIOCATALYTIC LACTONIZATION OF SYN-3,5-DIHYDROXY ESTERS [J].
BONINI, C ;
PUCCI, P ;
VIGGIANI, L .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :4050-4052
[2]   1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES [J].
CHEN, KM ;
HARDTMANN, GE ;
PRASAD, K ;
REPIC, O ;
SHAPIRO, MJ .
TETRAHEDRON LETTERS, 1987, 28 (02) :155-158
[3]   MONACOLIN-K, A NEW HYPOCHOLESTEROLEMIC AGENT PRODUCED BY A MONASCUS SPECIES [J].
ENDO, A .
JOURNAL OF ANTIBIOTICS, 1979, 32 (08) :852-854
[4]   ML-236A, ML-236B, AND ML-236C, NEW INHIBITORS OF CHOLESTEROGENESIS PRODUCED BY PENICILLIUM CITRINUM [J].
ENDO, A ;
KURODA, M ;
TSUJITA, Y .
JOURNAL OF ANTIBIOTICS, 1976, 29 (12) :1346-1348
[5]   ENZYMATIC LACTONIZATION OF GAMMA-HYDROXYESTERS IN ORGANIC-SOLVENTS - SYNTHESIS OF OPTICALLY PURE GAMMA-METHYLBUTYROLACTONES AND GAMMA-PHENYLBUTYROLACTONE [J].
GUTMAN, AL ;
ZUOBI, K ;
BOLTANSKY, A .
TETRAHEDRON LETTERS, 1987, 28 (33) :3861-3864
[6]  
HENKEL B, 1992, LIEBIGS ANN CHEM, P809
[7]   ENZYMES IN ORGANIC-SYNTHESIS .16. ENZYME-CATALYZED LACTONIZATION OF METHYL (+/-)-(E)-3,5-DIHYDROXY-7-PHENYL-6-HEPTENOATES - A COMPARISON OF THE BEHAVIOR OF SYN-COMPOUNDS AND ANTI-COMPOUNDS [J].
HENKEL, B ;
KUNATH, A ;
SCHICK, H .
TETRAHEDRON-ASYMMETRY, 1993, 4 (02) :153-156
[8]  
OZEGOWSKI R, IN PRESS LIEBIGS ANN