Synthetic methods.: 54.: Asymmetric syntheses of N-acetyl-(R)-coniine and N-boc-(2R,6R)-solenopsin A via ring-closing metathesis

被引:58
作者
Kumareswaran, R [1 ]
Hassner, A [1 ]
机构
[1] Bar Ilan Univ, Dept Chem, IL-52900 Ramat Gan, Israel
关键词
D O I
10.1016/S0957-4166(01)00411-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Asymmetric syntheses of piperidine alkaloids N-acetyl-(R)-coniine and (2R,6R)-trans-solenopsin were achieved utilizing stereoselective additions of allylphenylsulfone to chiral alkyl-N-sulfinylimines and ring-closing olefin metathesis. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2269 / 2276
页数:8
相关论文
共 23 条
[1]   Enantioselective synthesis of the trans-2,6-dialkylpiperidine alkaloids (2R,6R)-lupetidine and (2R,6R)-solenopsin A [J].
Amat, M ;
Hidalgo, J ;
Llor, N ;
Bosch, J .
TETRAHEDRON-ASYMMETRY, 1998, 9 (14) :2419-2422
[2]   Asymmetric routes to substituted piperidines [J].
Bailey, PD ;
Millwood, PA ;
Smith, PD .
CHEMICAL COMMUNICATIONS, 1998, (06) :633-640
[3]   Asymmetric synthesis of functionalized piperidine derivatives:: synthesis of (S)-anatabine [J].
Balasubramanian, T ;
Hassner, A .
TETRAHEDRON-ASYMMETRY, 1998, 9 (13) :2201-2205
[4]   Stereochemistry .87. Synthesis of chiral non-racemic 2-arylpyrrolines by a [3+2] cycloaddition route [J].
Balasubramanian, T ;
Hassner, A .
TETRAHEDRON LETTERS, 1996, 37 (32) :5755-5758
[5]   ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - SYNTHESES OF DIASTEREOISOMERS FROM BOC DERIVATIVES OF CYCLIC AMINES [J].
BEAK, P ;
LEE, WK .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1109-1117
[6]   A new asymmetric synthesis of (S)-(+)-pipecoline and (S)-(+)- and (R)-(-)-coniine by reductive photocyclization of dienamides [J].
Bois, F ;
Gardette, D ;
Gramain, JC .
TETRAHEDRON LETTERS, 2000, 41 (45) :8769-8772
[7]   Asymmetric synthesis and properties of sulfinimines (thiooxime S-oxides) [J].
Davis, FA ;
Reddy, RE ;
Szewczyk, JM ;
Reddy, GV ;
Portonovo, PS ;
Zhang, HM ;
Fanelli, D ;
Reddy, RT ;
Zhou, P ;
Carroll, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2555-2563
[8]   Improved synthesis of enantiopure sulfinimines (thiooxime S-oxides) from p-toluenesulfinamide and aldehydes and ketones [J].
Davis, FA ;
Zhang, YL ;
Andemichael, Y ;
Fang, TA ;
Fanelli, DL ;
Zhang, HM .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1403-1406
[9]  
ENDERS D, 1993, LIEBIGS ANN CHEM, P173
[10]  
Eskici M, 2000, SYNLETT, P1360