Asymmetric syntheses of (-)-epi-pseudoconhydrine and (-)-5-hydroxysedamine based on a cis-diastereoselective 1,4-asymmetric induction

被引:15
作者
Liu, Gang
Meng, Jie
Feng, Chen-Guo
Huang, Pei-Qiang [1 ]
机构
[1] Xiamen Univ, Coll Chem & Chem Engn, Dept Chem, Xiamen 361005, Fujian, Peoples R China
关键词
D O I
10.1016/j.tetasy.2008.05.002
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The asymmetric syntheses of (-)-epi-pseudoconhydrine and (-)-5-hydroxysedamine are reported. The key to these syntheses is an unusual highly cis-diastereoselective 1,4-asymmetric induction in the alpha-amidoallylation of the new chiral building block 15. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1297 / 1303
页数:7
相关论文
共 82 条
[61]   HYDROBORATION OF ENECARBAMATES AND THE SYNTHESIS OF BETA-HYDROXYPIPERIDINE ALKALOIDS [J].
PLEHIERS, M ;
HOOTELE, C .
TETRAHEDRON LETTERS, 1993, 34 (47) :7569-7570
[62]   Synthesis of beta-hydroxypiperidine alkaloids by anodic oxidation of carbamates and hydroboration [J].
Plehiers, M ;
Hootele, C .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1996, 74 (12) :2444-2453
[63]   ENANTIOMERICALLY PURE PYRROLIDINE DERIVATIVES FROM TRANS-4-HYDROXY-L-PROLINE BY ELECTROCHEMICAL OXIDATIVE DECARBOXYLATION AND TITANIUM-TETRACHLORIDE-MEDIATED REACTION WITH NUCLEOPHILES [J].
RENAUD, P ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1986, 69 (07) :1704-1710
[64]   A NEW ALKALOID FROM SOUTH-AFRICAN CONIUM SPECIES [J].
ROBERTS, MF ;
BROWN, RT .
PHYTOCHEMISTRY, 1981, 20 (03) :447-449
[65]   Chiral heterocycles by iminium ion cyclization [J].
Royer, J ;
Bonin, M ;
Micouin, L .
CHEMICAL REVIEWS, 2004, 104 (05) :2311-2352
[66]   Novel reduction of 3-hydroxypyridine and its use in the enantioselective synthesis of (+)-pseudoconhydrine and (+)-N-methylpseudoconhydrine [J].
Sakagami, H ;
Kamikubo, T ;
Ogasawara, K .
CHEMICAL COMMUNICATIONS, 1996, (12) :1433-1434
[67]  
Schneider M. J., 1996, ALKAL CHEM, V10, P155
[68]   ELECTROORGANIC CHEMISTRY .113. SYNTHESIS OF (+)-N-METHYLPSEUDOCONHYDRINE AND (-)-N-METHYLPSEUDOCONHYDRINE FROM L-LYSINE USING ANODIC-OXIDATION AS THE KEY REACTION [J].
SHONO, T ;
MATSUMURA, Y ;
ONOMURA, O ;
SATO, M .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4118-4121
[69]   New developments in the chemistry of N-acyliminium ions and related intermediates [J].
Speckamp, WN ;
Moolenaar, MJ .
TETRAHEDRON, 2000, 56 (24) :3817-3856
[70]   INTRAMOLECULAR REACTIONS OF N-ACYLIMINIUM INTERMEDIATES [J].
SPECKAMP, WN ;
HIEMSTRA, H .
TETRAHEDRON, 1985, 41 (20) :4367-4416