A SHORT AND EFFICIENT SYNTHESIS OF (-)-METHYL 8-EPI-NONACTATE

被引:15
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
10.1016/0040-4039(93)85020-W
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(-)-Methyl 8-epi-nonactate has been synthesized from (-)-5-hydroxymethyl-3-methyl-2-isoxazoline in seven synthetic steps in 26% overall yield.
引用
收藏
页码:1609 / 1610
页数:2
相关论文
共 15 条
[1]   SYNTHESIS OF (+/-)-NONACTIC ACID [J].
ARCO, MJ ;
TRAMMELL, MH ;
WHITE, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (12) :2075-2083
[2]   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
[3]   A STEREOCONTROLLED SYNTHESIS OF THE METHYL-ESTER OF (+/-)-NONACTIC ACID [J].
BARTLETT, PA ;
JERNSTEDT, KK .
TETRAHEDRON LETTERS, 1980, 21 (17) :1607-1610
[4]   CONVENIENT PREPARATION OF TETRAHYDROFURYLIDENE ACETATES [J].
BRYSON, TA .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (19) :3428-3429
[5]  
Corey E. J., 1989, LOGIC CHEM SYNTHESIS
[7]   TOTAL SYNTHESIS OF (+/-)-VERNOLEPIN [J].
KIECZYKOWSKI, GR ;
SCHLESSINGER, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (06) :1938-1940
[8]   ASYMMETRIC SILYL NITRONATE CYCLOADDITIONS WITH BORNANE-10,2-SULTAM DERIVATIVES [J].
KIM, BH ;
LEE, JY .
TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1359-1370
[9]   ASYMMETRIC INDUCTION IN SILYL NITRONATE CYCLOADDITIONS TO OPPOLZER CHIRAL SULTAM DERIVATIVES [J].
KIM, BH ;
LEE, JY ;
KIM, KM ;
WHANG, DM .
TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :27-30
[10]   ENANTIOSELECTIVE SYNTHESES OF (+)-METHYL NONACTATE AND (-)-METHYL 8-EPI-NONACTATE VIA ASYMMETRIC CYCLOADDITIVE ROUTE [J].
KIM, BH ;
LEE, JY .
TETRAHEDRON LETTERS, 1992, 33 (18) :2557-2560