ENZYME CATALYZED LACTONIZATION OF 3,5 DIHYDROXY ESTERS - ENANTIOSELECTIVE SYNTHESIS OF NATURALLY-OCCURRING 3-HYDROXY-5-DECANOLIDE, (-)-MASSOIALACTONE, AND 3-HYDROXY-5-ICOSANOLIDE

被引:24
作者
BONINI, C
PUCCI, P
RACIOPPI, R
VIGGIANI, L
机构
[1] Dipartimento di Chimica, Università della Basilicata, 85100 Potenza
关键词
D O I
10.1016/S0957-4166(00)82308-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Synthesis of optically active (+)-3-hydroxy-5-decanolide, (-)-massoialactone and of the recently isolated 3-hydroxy-5-icosanolide was achieved by enzyme-catalysed lactonization of racemic 3,5 dihydroxy esters with PPL in dry Et2O . Ees vary from 86% up to > 98%.
引用
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页码:29 / 32
页数:4
相关论文
共 18 条
[1]   CD OF ALPHA-BETA-UNSATURATED LACTONES [J].
BEECHAM, AF .
TETRAHEDRON, 1972, 28 (22) :5543-+
[2]  
BENNETT F, 1989, HETEROCYCLES, V29, P639
[3]   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
[4]  
Brand J M, 1979, Fortschr Chem Org Naturst, V37, P1
[5]   INSECT VENOMS ATTRACTANTS AND REPELLENTS .11. MASSOILACTONE FROM 2 SPECIES OF FORMICINE ANTS AND SOME OBSERVATIONS ON CONSTITUENTS OF BARK OIL OF CRYPTOCARYA MASSOIA [J].
CAVILL, GWK ;
CLARK, DV ;
WHITFIELD, FB .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1968, 21 (11) :2819-+
[6]   A NOVEL METHOD FOR THE INSITU GENERATION OF ALKOXYDIALKYLBORANES AND THEIR USE IN THE SELECTIVE PREPARATION OF 1,3-SYN DIOLS [J].
CHEN, KM ;
GUNDERSON, KG ;
HARDTMANN, GE ;
PRASAD, K ;
REPIC, O ;
SHAPIRO, MJ .
CHEMISTRY LETTERS, 1987, (10) :1923-1926
[7]  
CROMBIE L, 1955, J CHEM SOC, P2535
[8]   BIOSYNTHESIS OF PARASORBIC ACID (HEX-2-EN-5-OLIDE) BY ROWAN BERRY (SORBUS AUCUPARIA L) [J].
CROMBIE, L ;
FIRTH, PA .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (22) :2852-&
[9]   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
[10]   SESQUITERPENE LACTONES AND A C-20 ALIPHATIC LACTONE FROM TEXAS BITTERWEED, HYMENOXYS-ODORATA [J].
GAO, F ;
WANG, HP ;
MABRY, TJ ;
WATSON, WH ;
KASHYAP, RP .
PHYTOCHEMISTRY, 1990, 29 (02) :551-560