A concise synthesis of turneforcidine via a metalloiminium ion cyclization terminated by the 2-(methylthio)-3-(trimethylsilyl)-1-propenyl moiety

被引:11
作者
An, DK [1 ]
Duncan, D [1 ]
Livinghouse, T [1 ]
Reid, P [1 ]
机构
[1] Montana State Univ, Dept Chem & Biochem, Bozeman, MT 59717 USA
关键词
D O I
10.1021/ol010122b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A concise synthetic route to racemic turneforcidine (1) is described that relies on the stereocontrolled cyclization of the 2-(methylthio)-3-(trimethylsilyi)-1-propenyl bearing imine 5 in the presence of TiCl4.
引用
收藏
页码:2961 / 2963
页数:3
相关论文
共 13 条
[1]  
CULVENOR CCJ, 1968, PYRROLIZIDINE ALKOID
[2]   THE TANDEM CYCLOADDITION CHEMISTRY OF NITROALKENES - A NOVEL SYNTHESIS OF (-)-HASTANECINE [J].
DENMARK, SE ;
THORARENSEN, A .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5672-5680
[3]   Tandem [4+2]/[3+2]cycloadditions of nitroalkenes .11. The synthesis of (+)-crotanecine [J].
Denmark, SE ;
Thorarensen, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (01) :125-137
[4]   Intramolecular cyclizations of imines bearing the 2-(thiomethyl)-3-trimethylsilyl-l-propenyl terminator. An efficient new procedure for the stereocontrolled synthesis of functionalized pyrrolidine derivatives [J].
Duncan, D ;
Livinghouse, T .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (15) :5237-5240
[5]   SILICON DIRECTED N-ACYLIMINIUM ION CYCLIZATIONS - HIGHLY SELECTIVE SYNTHESES OF (+/-)-ISORETRONECANOL AND (+/-)-EPILUPININE [J].
HIEMSTRA, H ;
SNO, MHAM ;
VIJN, RJ ;
SPECKAMP, WN .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (21) :4014-4020
[6]   INTRAMOLECULAR ALLYLSTANNANE CYCLIZATIONS IN ALKALOID SYNTHESIS - APPLICATIONS TO PYRROLIZIDINE ALKALOIDS [J].
KECK, GE ;
CRESSMAN, ENK ;
ENHOLM, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (18) :4345-4349
[7]   Stereocontrolled synthesis of 5-acyl-3,4-dihydro-2H-pyrroles and related heterocycles via intramolecular 2-propylidene-1,3-bis(silane)-acylnitrilium ion cyclizations [J].
Kercher, T ;
Livinghouse, T .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :805-812
[8]   Intramolecular 2-propylidene-1,3-bis(silane) imine cyclizations. An efficient new procedure for the stereocontrolled synthesis of pyrrolidines, isotropanes, and bridged pyrrolizidines [J].
Kercher, T ;
Livinghouse, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (17) :4200-4201
[9]   Homoproline homologation by enolate Claisen rearrangement or direct allylation: syntheses of (-)-trachelanthamidine, (-)-isoretronecanol and (+/-)-turneforcidine [J].
Knight, DW ;
Share, AC ;
Gallagher, PT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (14) :2089-2097
[10]  
Mattocks AR., 1986, CHEM TOXICOLOGY PYRR