Cascade iminium ion reactions for the facile synthesis of quinolizidines.: Concise syntheses of (±)-epilupinine and (-)-epimyrtine

被引:41
作者
Amorde, SM [1 ]
Judd, AS [1 ]
Martin, SF [1 ]
机构
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
关键词
D O I
10.1021/ol050544b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several novel cascade processes have been designed and developed that involve sequential reactions of imines and iminium ions to form substituted quinolizidine ring systems in a single step from simple and readily available starting materials. The utility and promise of these cascade reactions is evident from their application to extraordinarily concise syntheses of the representative quinolizidine alkaloids epilupinine and (-)-epimyrtine.
引用
收藏
页码:2031 / 2033
页数:3
相关论文
共 38 条
[1]   The intriguing reactivity of functionalized β-amino alcohols with glyoxal:: Application to a new expedient enantioselective synthesis of trans-6-alkylpipecolic acids [J].
Agami, C ;
Comesse, S ;
Kadouri-Puchot, C .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2424-2428
[2]   A concise synthesis of turneforcidine via a metalloiminium ion cyclization terminated by the 2-(methylthio)-3-(trimethylsilyl)-1-propenyl moiety [J].
An, DK ;
Duncan, D ;
Livinghouse, T ;
Reid, P .
ORGANIC LETTERS, 2001, 3 (19) :2961-2963
[3]   VINYLSILANE-TERMINATED AND ALKYNYLSILANE-TERMINATED CYCLIZATION REACTIONS [J].
BLUMENKOPF, TA ;
OVERMAN, LE .
CHEMICAL REVIEWS, 1986, 86 (05) :857-873
[4]   Cascade radical cyclisations of imines [J].
Bowman, WR ;
Stephenson, PT ;
Young, AR .
TETRAHEDRON, 1996, 52 (35) :11445-11462
[5]   Enantioselective synthesis of 5-substituted pipecolic acids using an intramolecular allylsilane-iminium ion cyclization [J].
Cellier, M ;
Gelas-Mialhe, Y ;
Husson, HP ;
Perrin, B ;
Remuson, R .
TETRAHEDRON-ASYMMETRY, 2000, 11 (19) :3913-3919
[6]   Nonstabilized N-unsubstituted azomethine ylides:: A synthesis of indolizidine 239CD [J].
Clark, RB ;
Pearson, WH .
ORGANIC LETTERS, 1999, 1 (02) :349-351
[7]   Asymmetric synthesis of the quinolizidine alkaloid (-)-epimyrtine with intramolecular Mannich Cyclization and n-sulfinyl δ-amino β-ketoesters [J].
Davis, FA ;
Mang, Y ;
Anilkumar, G .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (21) :8061-8064
[8]   Biomimetic entry to the sarpagan family of indole alkaloids:: Total synthesis of (+)-geissoschizine and (+)-N-methylvellosimine [J].
Deiters, A ;
Chen, K ;
Eary, CT ;
Martin, SF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (15) :4541-4550
[9]   Stereoselective total synthesis of dihydrocorynantheol [J].
Deiters, A ;
Martin, SF .
ORGANIC LETTERS, 2002, 4 (19) :3243-3245
[10]  
Deslongchamps P., 1983, ORGANIC CHEM SERIES, V1