ENANTIOSELECTIVE SYNTHESES OF (+)-METHYL NONACTATE AND (-)-METHYL 8-EPI-NONACTATE VIA ASYMMETRIC CYCLOADDITIVE ROUTE

被引:30
作者
KIM, BH
LEE, JY
机构
[1] Department of Chemistry, Center for Biofunctional Molecules, Pohang Institute of Science and Technology, Pohang, 790-600
关键词
D O I
10.1016/S0040-4039(00)92241-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantioselective routes to (+)-methyl nonactate (2) and (-)-methyl 8-epi-nonactate (3) are described. The cornerstone of this synthetic strategy is a combination of asymmetric silyl nitronate cycloaddition and asymmetric reduction, which provides the key syn-1.3-diol intermediate 4.
引用
收藏
页码:2557 / 2560
页数:4
相关论文
共 44 条
[1]   SYNTHESIS OF (+/-)-NONACTIC ACID [J].
ARCO, MJ ;
TRAMMELL, MH ;
WHITE, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (12) :2075-2083
[2]   STEREOSELECTIVE SYNTHESIS OF (+/-)-METHYL NONACTATE [J].
BALDWIN, SW ;
MCIVER, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :320-322
[3]   A CONCISE SYNTHESIS OF (+/)-TERT-BUTYL 8-ORTHO-TERT-BUTYLDIMETHYLSILYLNONACTATE [J].
BARRETT, AGM ;
SHETH, HG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (03) :170-172
[4]   STUDIES ON THE NACTINS - TOTAL SYNTHESIS OF (+/-)-TERT-BUTYL 8-O-(TERT-BUTYLDIMETHYLSILYL)NONACTATE [J].
BARRETT, AGM ;
SHETH, HG .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) :5017-5022
[5]   ENANTIODIVERGENT SYNTHESES OF (+)-NONACTIC AND (-)-NONACTIC ACID AND THE TOTAL SYNTHESIS OF NONACTIN [J].
BARTLETT, PA ;
MEADOWS, JD ;
OTTOW, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (18) :5304-5311
[6]   A STEREOCONTROLLED SYNTHESIS OF THE METHYL-ESTER OF (+/-)-NONACTIC ACID [J].
BARTLETT, PA ;
JERNSTEDT, KK .
TETRAHEDRON LETTERS, 1980, 21 (17) :1607-1610
[7]   THE SYNTHESIS OF (+)-TERT-BUTYL AND (-)-TERT-BUTYL NONACTATE FROM L-GLUTAMIC ACID [J].
BATMANGHERLICH, S ;
DAVIDSON, AH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (20) :1399-1401
[8]   DIASTEREOMERS OF NONACTIN ACID AND EPIMERS OF 2-DESMETHYLNONACTIN ACID [J].
BECK, G ;
HENSELEIT, E .
CHEMISCHE BERICHTE-RECUEIL, 1971, 104 (01) :21-+
[9]  
BULMAN PPC, 1985, J CHEM SOC CHEM COMM, P822
[10]   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