AN ASYMMETRIC-SYNTHESIS OF (R)-(+)-2-NONYL-2-(CARBOMETHOXY)-CYCLOPENTANONE, A KNOWN PRECURSOR OF THE ANTIBIOTIC (-)-MALYNGOLIDE

被引:31
作者
GUINGANT, A
机构
[1] Unite de Chimie Organique associée au CNRS, ESPCI, 75231 Paris Cedex 05
关键词
CHIRAL BETA-ENAMINO ESTER; ASYMMETRIC SYNTHESIS; LEWIS ACID; (-)MALYNGOLIDE;
D O I
10.1016/S0957-4166(00)82165-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A synthesis of (R)-(+)-2-nonyl-2-(carbomethoxy)cyclopentanone 2 via an asymmetric Michael process involving the chiral beta-enamino ester (+)-3 is described.
引用
收藏
页码:415 / 418
页数:4
相关论文
共 16 条
[1]   STRUCTURE AND ABSOLUTE-CONFIGURATION OF MALYNGOLIDE, AN ANTIBIOTIC FROM THE MARINE BLUE-GREEN-ALGA LYNGBYA-MAJUSCULA GOMONT [J].
CARDLLINA, JH ;
MOORE, RE ;
ARNOLD, EV ;
CLARDY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4039-4042
[2]  
GIESE B, 1987, LIEBIGS ANN CHEM, P231
[3]   SYNTHESIS OF OPTICALLY-ACTIVE ALPHA,ALPHA-DISUBSTITUTED BETA-KETO-ESTERS VIA CHIRAL BETA-ENAMINO ESTERS [J].
GUINGANT, A ;
HAMMAMI, H .
TETRAHEDRON-ASYMMETRY, 1991, 2 (06) :411-414
[4]   STEREOSELECTIVE SYNTHESIS OF MARINE ANTIBIOTIC (-)-MALYNGOLIDE AND ITS STEREOISOMERS [J].
ICHIMOTO, I ;
MACHIYA, K ;
KIRIHATA, M ;
UEDA, H .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (03) :657-662
[5]  
KOGURE T, 1984, J ORG CHEM, V49, P578
[6]   SYNTHESIS OF (-)-MALYNGOLIDE FROM D-LACTOSE [J].
MATSUO, K ;
HASUIKE, Y ;
KADO, H .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (10) :2847-2849
[7]   N-METHOXY-N-METHYLAMIDES AS EFFECTIVE ACYLATING AGENTS [J].
NAHM, S ;
WEINREB, SM .
TETRAHEDRON LETTERS, 1981, 22 (39) :3815-3818
[8]  
PUGNY JR, 1982, TETRAHEDRON LETT, V23, P4929
[9]   AN ASYMMETRIC TOTAL SYNTHESIS OF A NEW MARINE ANTIBIOTIC-MALYNGOLIDE [J].
SAKITO, Y ;
TANAKA, S ;
ASAMI, M ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1980, (10) :1223-1226
[10]  
SATO T, 1988, CHEM LETT, P3739