Highly stereoselective [4+3] cycloadditions of nitrogen-stabilized oxyallyl cations with pyrroles. An approach to parvineostemonine

被引:62
作者
Antoline, Jennifer E.
Hsung, Richard P.
Huang, Jian
Song, Zhenlei
Li, Gang
机构
[1] Univ Wisconsin, Div Pharmaceut Sci, Madison, WI 53705 USA
[2] Univ Wisconsin, Dept Chem, Madison, WI 53705 USA
关键词
D O I
10.1021/ol070103n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly stereoselective [4 + 3] cycloaddition of N-substituted pyrroles with allenamide-derived nitrogen-stabilized chiral oxyallyl cations is described here. This method provides an approach for constructing tropinone alkaloids.
引用
收藏
页码:1275 / 1278
页数:4
相关论文
共 72 条
[1]   Addition of a chiral copper reagent derived from propargylic oxazolidininone to aldehydes [J].
Alouane, N ;
Bernaud, F ;
Marrot, J ;
Vrancken, E ;
Mangeney, P .
ORGANIC LETTERS, 2005, 7 (26) :5797-5800
[2]  
[Anonymous], 1997, Organic Reactions
[3]  
[Anonymous], [No title captured]
[4]   Stereoselective preparation of (Z)-2-(trialkylsilyloxy)-2-alkenals by retrocycloaddition reactions of 4H-4-alkyl-5-(trialkylsilyloxy)-1,3-dioxins.: Useful reactants for Lewis acid catalyzed [4+3] cyclizations [J].
Aungst, RA ;
Funk, RL .
ORGANIC LETTERS, 2001, 3 (22) :3553-3555
[5]   High regio-, chemo-, and stereoselectivity via low-temperature 4+3 cycloadditions.: Convergent synthesis of multifunctionalized vinylmetals (M = Si, Sn) and S-vinyl benzenecarbothioates [J].
Beck, H ;
Stark, CBW ;
Hoffmann, HMR .
ORGANIC LETTERS, 2000, 2 (07) :883-886
[6]   Syntheses of 2,5-disubstituted dihydrofurans from γ-substituted chiral allenamides [J].
Berry, CR ;
Hsung, RP ;
Antoline, JE ;
Petersen, ME ;
Challeppan, R ;
Nielson, JA .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4038-4042
[7]   TOTAL SYNTHESIS OF DL-STENINE [J].
CHEN, CY ;
HART, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6236-6240
[8]   Diastereocontrol of [4+3] cyclic oxyallyl cycloadditions by alkoxy substituents [J].
Cho, SY ;
Lee, JC ;
Cha, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3394-3395
[9]  
CLOSE WJ, 1950, J ORG CHEM, V15, P1131
[10]   Acid-promoted retro-Mannich reaction of N-protected tropenones to 2-substituted pyrroles [J].
Cramer, N ;
Juretschke, J ;
Laschat, S ;
Baro, A ;
Frey, W .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (07) :1397-1400