5,6-dihydroindolizines as convenient precursors of indolizidine 167B and analogues

被引:10
作者
Guazzelli, G [1 ]
Lazzaroni, R [1 ]
Settambolo, R [1 ]
机构
[1] Univ Pisa, Dipartimento Chim & Chim Ind, CNR, ICCOM, I-56126 Pisa, Italy
来源
SYNTHESIS-STUTTGART | 2005年 / 18期
关键词
(-)-indolizidine 16713; 5,6-dihydroindolizines; synthesis; 4-(pyrrol-l-yl)butanal; enantioselective hydrogenation;
D O I
10.1055/s-2005-918407
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Starting from 5-carboxyethyl-5,6-dihydroindolizine, the title alkaloid was obtained in 25% overall yield via differently C5-substituted 5,6-dihydroindolizines and final exhaustive hydrogenation. An alternative strategy for the synthesis of optically active indolizidine 167B and analogues still based on 5,6-dihydroindolizine intermediates is given.
引用
收藏
页码:3119 / 3123
页数:5
相关论文
共 19 条
[1]  
[Anonymous], 1993, ALKALOIDS CHEM PHARM
[2]   INTERACTION OF GEPHYROTOXIN AND INDOLIZIDINE ALKALOIDS WITH THE NICOTINIC ACETYLCHOLINE RECEPTOR-ION CHANNEL COMPLEX OF TORPEDO ELECTROPLAX [J].
ARONSTAM, RS ;
DALY, JW ;
SPANDE, TF ;
NARAYANAN, TK ;
ALBUQUERQUE, EX .
NEUROCHEMICAL RESEARCH, 1986, 11 (08) :1227-1240
[3]   Convenient new route to piperidines, pyrrolizidines, indolizidines, and quinolizidines by cyclization of acetylenic sulfones with β- and γ-chloroamines.: Enantioselective total synthesis of indolizidines (-)-167B, (-)-209D, (-)-209B, and (-)-207A [J].
Back, TG ;
Nakajima, K .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4543-4552
[4]   Enantioselective synthesis of (-)-indolizidine 167B [J].
Chalard, P ;
Remuson, R ;
Gelas-Mialhe, Y ;
Gramain, JC ;
Canet, I .
TETRAHEDRON LETTERS, 1999, 40 (09) :1661-1664
[5]   A radical approach towards indolizidine 167B [J].
Corvo, MC ;
Pereira, MMA .
TETRAHEDRON LETTERS, 2002, 43 (03) :455-458
[6]  
Daly JW, 1999, ALKAL CHEM, V13, P1, DOI 10.1016/S0735-8210(99)80024-7
[7]   FURTHER CLASSIFICATION OF SKIN ALKALOIDS FROM NEOTROPICAL POISON FROGS (DENDROBATIDAE), WITH A GENERAL SURVEY OF TOXIC NOXIOUS SUBSTANCES IN THE AMPHIBIA [J].
DALY, JW ;
MYERS, CW ;
WHITTAKER, N .
TOXICON, 1987, 25 (10) :1023-1095
[8]   IMPROVED CARBON-CARBON LINKING BY CONTROLLED COPPER CATALYSIS [J].
FOUQUET, G ;
SCHLOSSE.M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1974, 13 (01) :82-83
[9]   Indolizidine and quinolizidine alkaloids [J].
Michael, JP .
NATURAL PRODUCT REPORTS, 2003, 20 (05) :458-475
[10]   A convenient allylsilane-N-acyliminium route toward 5-alkylindolizidines.: Diastereoselective synthesis of (±)-indolizidine 167B [J].
Peroche, S ;
Remuson, R ;
Gelas-Mialhe, Y ;
Gramain, JC .
TETRAHEDRON LETTERS, 2001, 42 (28) :4617-4619