ASYMMETRIC-SYNTHESIS WITH ALPHA,BETA-BIS[(METHOXYMETHYL)OXY] KETONES - ENANTIOSELECTIVE TOTAL SYNTHESIS OF NATURAL (+)-INDOLIZIDINE-195B (BICYCLIC GEPHYROTOXIN-195B) AND (-)-PINIDINE AND THEIR ENANTIOMERS FROM A COMMON CHIRAL SYNTHON

被引:109
作者
YAMAZAKI, N [1 ]
KIBAYASHI, C [1 ]
机构
[1] TOKYO COLL PHARM,HACHIOJI,TOKYO 19203,JAPAN
关键词
D O I
10.1021/ja00186a038
中图分类号
O6 [化学];
学科分类号
0703 ;
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页码:1396 / 1408
页数:13
相关论文
共 26 条
[1]  
ANH NT, 1977, NOUV J CHIM, V1, P61
[2]   AN EFFICIENT SYNTHESIS OF (+/-)-PINIDINE [J].
ARSENIYADIS, S ;
SARTORETTI, J .
TETRAHEDRON LETTERS, 1985, 26 (06) :729-732
[3]   2-CYANO DELTA-3 PIPERIDINES .6. A GENERAL-METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF CIS AND TRANS 2,6-DIALKYLPIPERIDINE ALKALOIDS [J].
BONIN, M ;
ROMERO, JR ;
GRIERSON, DS ;
HUSSON, HP .
TETRAHEDRON LETTERS, 1982, 23 (33) :3369-3372
[4]  
CHEREST M, 1968, TETRAHEDRON LETT, P2199
[5]   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-&
[6]   A NEW, STEREOSPECIFIC OLEFIN SYNTHESIS FROM 1,2-DIOLS [J].
COREY, EJ ;
WINTER, RAE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (17) :2677-&
[7]  
DALY JW, 1986, ALKALOIDS CHEM BIOL, V4, pCH1
[8]  
ELIEL EL, 1983, ASYMMETRIC SYNTHESIS, V2, pCH5
[9]   HIGHLY DIASTEREOCONTROLLED REDUCTION OF KETONES BY MEANS OF HYDROSILANES - PRACTICAL SYNTHESIS OF OPTICALLY-ACTIVE 1,2-DIOLS AND 2-AMINO ALCOHOLS OF THREO OR ERYTHRO CONFIGURATION [J].
FUJITA, M ;
HIYAMA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (16) :4629-4630
[10]  
GAREGG PJ, 1979, SYNTHESIS-STUTTGART, V469, P813