EFFICIENT ASYMMETRIC-SYNTHESIS OF INDOLIZIDINE BUILDING-BLOCKS

被引：27

作者：

BOND, TJ ^{[1
]}

JENKINS, R ^{[1
]}

RIDLEY, AC ^{[1
]}

TAYLOR, PC ^{[1
]}

机构：

[1] UNIV WARWICK,DEPT CHEM,COVENTRY CV4 7AL,W MIDLANDS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 19期

关键词：

D O I：

10.1039/p19930002241

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular Friedel-Crafts acylation of a pyrrole derived from L-glutamic acid, followed by a highly selective hydrogenation, leads to either of the optically pure indolizidine alkaloid precursors 6 or 7, depending on the catalyst.

引用

页码：2241 / 2242

页数：2

共 17 条

[1]

BOX SJ, 1981, TETRAHEDRON LETT, V22, P2393

[2] N-ACYLDIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - A SHORT SYNTHESIS OF (+/-)-INDOLIZIDINE-209B [J].

COMINS, DL ;

ZELLER, E .

TETRAHEDRON LETTERS, 1991, 32 (42) :5889-5892

[3] 5,8-DISUBSTITUTED INDOLIZIDINES - A NEW CLASS OF NONCOMPETITIVE BLOCKERS FOR NICOTINIC RECEPTOR-CHANNELS [J].

DALY, JW ;

NISHIZAWA, Y ;

PADGETT, WL ;

TOKUYAMA, T ;

SMITH, AL ;

HOLMES, AB ;

KIBAYASHI, C ;

ARONSTAM, RS .

NEUROCHEMICAL RESEARCH, 1991, 16 (11) :1213-1218

[4] 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

[5]

DALY JW, 1982, PROGR CHEM ORGANIC N, V41, P205

[6] ENANTIOSELECTIVE SYNTHESIS OF (5R,9R)-5-PROPYL-OCTAHYDROINDOLIZINE [(-)-GEPHYROTOXIN 167B] [J].

FLEURANT, A ;

CELERIER, JP ;

LHOMMET, G .

TETRAHEDRON-ASYMMETRY, 1992, 3 (06) :695-696

[7]

HOLMES AB, 1991, J ORG CHEM, V56, P643

[8] SHORT, ENANTIOGENIC SYNTHESES OF (-)-INDOLIZIDINE 167B AND (+)-MONOMORINE [J].

JEFFORD, CW ;

TANG, Q ;

ZASLONA, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (09) :3513-3518

[9] ENANTIOSPECIFIC SYNTHESES OF INDOLIZIDINE-167B AND INDOLIZIDINE-209D [J].

JEFFORD, CW ;

WANG, JB .

TETRAHEDRON LETTERS, 1993, 34 (19) :3119-3122

[10]

KASHIMA C, 1988, J CHEM RES-S, P62

← 1 2 →