ENZYMATIC-HYDROLYSIS OF CYCLOPROPANES - TOTAL SYNTHESIS OF OPTICALLY PURE DICTYOPTERENE-A AND DICTYOPTERENE-C'

被引:66
作者
GRANDJEAN, D
PALE, P
CHUCHE, J
机构
[1] Laboratoire de chimie organique physique, URA CNRS 459 Université de Reims-Champagne-Ardenne
关键词
D O I
10.1016/S0040-4020(01)86378-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enzymatic hydrolysis of cis-1,2-bis(butyryloxymethyl)cyclopropane 3 under optimized conditions gives, in quantitative yield, optically pure cis-(1S,2R)-1-hydroxymethyl-2-butyryloxymethylcyclopropane 1. This compound is a versatile cyclopropane synthon as exemplified by the total synthesis of optically pure seaweed pheromones Dictyopterenes A and C'.
引用
收藏
页码:1215 / 1230
页数:16
相关论文
共 29 条
[1]   ENZYMATIC ESTER HYDROLYSIS AND SYNTHESIS - 2 APPROACHES TO CYCLOALKANE DERIVATIVES OF HIGH ENANTIOMERIC PURITY [J].
ADER, U ;
BREITGOFF, D ;
KLEIN, P ;
LAUMEN, KE ;
SCHNEIDER, MP .
TETRAHEDRON LETTERS, 1989, 30 (14) :1793-1796
[2]  
BESTMANN HJ, 1974, SYNTHESIS-STUTTGART, P798
[3]   SYNTHESIS OF (+/-)-DICTYOPTERENE A AND (+/-)-DICTYOPTERENE C' [J].
BILLUPS, WE ;
CHOW, WY ;
CROSS, JH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (07) :252-252
[4]   SYNTHESIS OF (+/-)-DESMARESTENE AND (+/-)-VIRIDIENE, THE 2 SPERM RELEASING AND ATTRACTING PHEROMONES FROM THE BROWN-ALGAE DESMARESTIA-ACULEATA AND DESMARESTIA-VIRIDIS [J].
BOLAND, W ;
JAKOBY, K ;
JAENICKE, L .
HELVETICA CHIMICA ACTA, 1982, 65 (07) :2355-2362
[5]   SYNTHESIS OF (+) DICTYOPTERENE A CONSTITUENT OF MARINE BROWN-ALGAE AND (+) DICTYOPTERENE C' BY CHIRALITY TRANSFER OF OPTICALLY-ACTIVE ALLYLIC BENZOATE WITH PALLADIUM (O) CATALYST [J].
COLOBERT, F ;
GENET, JP .
TETRAHEDRON LETTERS, 1985, 26 (23) :2779-2782
[6]   SYNTHESIS OF SUBSTITUTED DIBENZOPHOSPHOLES .1. [J].
CORNFORTH, J ;
CORNFORTH, RH ;
GRAY, RT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (10) :2289-2297
[7]  
DORCH D, 1985, TETRAHEDRON LETT, V26, P3319
[8]   ANNULATED PYRANOSIDES .5. AN ENANTIOSPECIFIC ROUTE TO (+) AND (-) CHRYSANTHEMUM DICARBOXYLIC-ACIDS [J].
FITZSIMMONS, BJ ;
FRASERREID, B .
TETRAHEDRON, 1984, 40 (08) :1279-1287
[9]   MOLECULAR SIEVE-ASSISTED OXIDATIONS - NEW METHODS FOR CARBOHYDRATE DERIVATIVE OXIDATIONS [J].
HERSCOVICI, J ;
ANTONAKIS, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (12) :561-562
[10]   SIGNAL SUBSTANCES AND THEIR RECEPTION IN THE SEXUAL CYCLE OF MARINE BROWN-ALGAE [J].
JAENICKE, L ;
BOLAND, W .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1982, 21 (09) :643-653