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

被引:18
作者
HENKEL, B [1 ]
KUNATH, A [1 ]
SCHICK, H [1 ]
机构
[1] CTR SELECT ORGAN SYNTH,RUDOWER CHAUSSEE 5,O-1199 BERLIN,GERMANY
关键词
D O I
10.1016/S0957-4166(00)82325-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
3-Hydroxy lactones with a high enantiomeric excess were obtained by the lipase-catalyzed enantioselective lactonization of racemic syn- and anti-3,5-dihydroxy carboxylic esters. The (5S)-lactones were formed predominantly from both diols with pancreatin as enzyme. The lipase from Candida sp. 382, however, catalyzed the preferential formation of the (5S)-lactone only from the syn-diol. From the anti-diol the (5R)-lactone was formed as the main enantiomer.
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页码:153 / 156
页数:4
相关论文
共 9 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]   CHEMISTRY, BIOCHEMISTRY, AND PHARMACOLOGY OF HMG-COA REDUCTASE INHIBITORS [J].
ENDO, A .
KLINISCHE WOCHENSCHRIFT, 1988, 66 (10) :421-427
[4]   MONACOLIN-K, A NEW HYPOCHOLESTEROLEMIC AGENT PRODUCED BY A MONASCUS SPECIES [J].
ENDO, A .
JOURNAL OF ANTIBIOTICS, 1979, 32 (08) :852-854
[5]   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
[6]  
HENKEL B, 1992, LIEBIGS ANN CHEM, P809
[7]  
MEYER HH, 1979, LIEBIGS ANN CHEM, P484
[8]   RECENT STUDIES ON VERATRUM ALKALOIDS - A NEW REACTION OF SODIUM TRIACETOXYBOROHYDRIDE [NABH(OAC)3] [J].
SAKSENA, AK ;
MANGIARACINA, P .
TETRAHEDRON LETTERS, 1983, 24 (03) :273-276
[9]  
SCHICK H, IN PRESS LIEBIGS ANN