Enantioselective synthesis of (-)-indolizidine 167B

被引：55
作者：
Chalard, P
Remuson, R [1 ]
Gelas-Mialhe, Y
Gramain, JC
Canet, I
机构：
[1] CNRS, F-63177 Clermont Ferrand, France
[2] Univ Blaise Pascal, F-63177 Clermont Ferrand, France
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 09期
关键词：
allylsilane; acyliminium ion; alkaloid; indolizidine;
D O I：
10.1016/S0040-4039(99)00059-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantioselective total synthesis of (-)-indolizidine 167B is described. The key step is the intramolecular cyclization of the chiral N-acyliminium ion 6. Indolizidine 167B was obtained in 7 steps and 17% yield from ethyl (R)-3-aminohexanoate, with an enantiomeric excess of 93%. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1661 / 1664
页数：4
相关论文
共 25 条
[1]   Synthesis of enantiopure indolizidine alkaloids from alpha-amino acids: Total synthesis of (-)-indolizidine 167B [J].
Angle, SR ;
Henry, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8549-8552
[2]  
Bardot V, 1998, HETEROCYCLES, V48, P507
[3]   ORIGINS OF THE HIGH STEREOSELECTIVITY IN THE CONJUGATE ADDITION OF LITHIUM(ALPHA-METHYLBENZYL)BENZYLAMIDE TO T-BUTYL CINNAMATE [J].
COSTELLO, JF ;
DAVIES, SG ;
ICHIHARA, O .
TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1999-2008
[4]  
CUNY GD, 1995, SYNLETT, P519
[5]  
Daly J W, 1982, PROGR CHEM ORGANIC N, V41, P205
[6]   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
[7]   ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS [J].
DAVIES, SG ;
ICHIHARA, O .
TETRAHEDRON-ASYMMETRY, 1991, 2 (03) :183-186
[8]   HIGHLY DIASTEREOSELECTIVE SYNTHESIS AND NMR CHARACTERIZATION OF NATURAL INDOLIZIDINE ALKALOIDS [J].
FLEURANT, A ;
SALIOU, C ;
CELERIER, JP ;
PLATZER, N ;
MOC, TV ;
LHOMMET, G .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (01) :255-258
[9]   ENANTIOSELECTIVE SYNTHESIS OF (5R,9R)-5-PROPYL-OCTAHYDROINDOLIZINE [(-)-GEPHYROTOXIN 167B] [J].
FLEURANT, A ;
CELERIER, JP ;
LHOMMET, G .
TETRAHEDRON-ASYMMETRY, 1992, 3 (06) :695-696
[10]   Enantioselective synthesis of the quinolizidine alkaloids (+)-myrtine and (-)-epimyrtine [J].
Gardette, D ;
Gelas-Mialhe, Y ;
Gramain, JC ;
Perrin, B ;
Remuson, R .
TETRAHEDRON-ASYMMETRY, 1998, 9 (10) :1823-1828
123