SYNTHESIS OF BRANCHED-CHAIN CYCLITOLS USING A PALLADIUM(0)-CATALYZED ALLYLIC COUPLING REACTION

被引:32
作者
BARTON, DHR
DALKO, P
GERO, SD
机构
[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE
[2] TEXAS A&M UNIV SYST,DEPT CHEM,COLLEGE STN,TX 77843
关键词
D O I
10.1016/S0040-4039(00)74357-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A carbanion derived from Meldrum's acid was used in a palladium(O)-catalysed allylic substitution reaction to prepare stereospecifically branched-chain cyclitols from the symmetrical 1,2,3,4,-tetraacetoxycyclohex-5-ene (4).
引用
收藏
页码:2471 / 2474
页数:4
相关论文
共 33 条
[11]   STEREOSPECIFIC SYNTHESES OF OLEFINS FROM 1,2-THIONOCARBONATES AND 1,2-TRITHIOCARBONATES . TRANS-CYCLOHEPTENE [J].
COREY, EJ ;
CAREY, FA ;
WINTER, RAE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (04) :934-&
[12]   A MILD PROCEDURE FOR THE CONVERSION OF 1,2-DIOLS TO OLEFINS [J].
COREY, EJ ;
HOPKINS, PB .
TETRAHEDRON LETTERS, 1982, 23 (19) :1979-1982
[13]  
COREY EJ, 1963, J AM CHEM SOC, V85, P267
[14]   (+/-)-1,2-4,5-DI-O-ISOPROPYLIDENE-MYO-INOSITOL [J].
GIGG, J ;
GIGG, R ;
PAYNE, S ;
CONANT, R .
CARBOHYDRATE RESEARCH, 1985, 142 (01) :132-134
[15]  
HECK RF, 1985, SERIES BEST SYNTHETI
[16]  
KOHN A, 1987, LIEBIGS ANN CHEM, P1045
[17]   THE USE OF INHIBITORS IN THE STUDY OF GLYCOSIDASES [J].
LALEGERIE, P ;
LEGLER, G ;
YON, JM .
BIOCHIMIE, 1982, 64 (11-1) :977-1000
[18]   SYNTHESIS OF (-)-CONDURITOL C (1L-CYCLOHEX-5-ENE-1,2,3/4-TETROL) [J].
LEDRIAN, C ;
VIEIRA, E ;
VOGEL, P .
HELVETICA CHIMICA ACTA, 1989, 72 (02) :338-347
[19]   ENANTIOMERICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES (NAKED SUGARS) AS SYNTHETIC INTERMEDIATES .11. TOTAL SYNTHESES OF (-)-CONDURITOL-B ((-)-1L-CYCLOHEX-5-ENE-1,3/2,4-TETROL) AND OF (+)-CONDURITOL-F ((+)-1D-CYCLOHEX-5-ENE-1,2,4/3-TETROL) - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF (+)-LEUCANTHEMITOL [J].
LEDRIAN, C ;
VIONNET, JP ;
VOGEL, P .
HELVETICA CHIMICA ACTA, 1990, 73 (01) :161-168
[20]   IMPROVED SYNTHESIS OF CONDURITOL-B EPOXIDE [J].
LEE, KJ ;
BOYD, SA ;
RADIN, NS .
CARBOHYDRATE RESEARCH, 1985, 144 (01) :148-154