The preparation of alpha-substituted, beta-hydroxy piperidines and pyrrolidines: The total synthesis of Febrifugine.

被引：71

作者：

Burgess, LE

Gross, EKM

Jurka, J

机构：

[1] Pfizer Inc., Central Research Division, Groton

[2] Amgen Boulder Inc., Boulder, CO 80301

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 19期

关键词：

D O I：

10.1016/0040-4039(96)00527-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Epoxides generated from cyclic ene carbamates are effective N-acyl iminium ion precursor and allow for the preparation of beta-hydroxy, alpha-substituted piperidines and pyrrolidines. The total synthesis of racemic Febrifugine is also described. (C) 1996 Elsevier Science Ltd.

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页码：3255 / 3258

页数：4

相关论文

共 25 条

[1] SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS [J].

ADAM, W ;

CHAN, YY ;

CREMER, D ;

GAUSS, J ;

SCHEUTZOW, D ;

SCHINDLER, M .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2800-2803

[2] SYNTHESIS OF A BICYCLIC GAMMA-LACTAM DIPEPTIDE ANALOG [J].

BALDWIN, JE ;

HULME, C ;

EDWARDS, AJ ;

SCHOFIELD, CJ ;

PARKES, KEB .

TETRAHEDRON LETTERS, 1993, 34 (10) :1665-1668

[3] STEREOCHEMISTRY OF FEBRIFUGINE .2. EVIDENCE FOR TRANS CONFIGURATION IN PIPERIDINE RING [J].

BARRINGER, DF ;

BERKELHA, G ;

WAYNE, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (10) :1937-1940

[4] STEREOCHEMISTRY OF FEBRIFUGINE .1. EQUILIBRIUM BETWEEN CIS-(3-SUBSTITUTED 2-PIPERIDYL)-2-PROPANONES TRANS-(3-SUBSTITUTED 2-PIPERIDYL)-2-PROPANONES [J].

BARRINGER, DF ;

BERKELHAMMER, G ;

CARTER, SD ;

GOLDMAN, L ;

LANZILOT, AE .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (10) :1933-1937

[5] CATIONIC CYCLIZATIONS OF KETENE DITHIOACETALS - A GENERAL-SYNTHESIS OF PYRROLIZIDINE, INDOLIZIDINE, AND QUINOLIZIDINE ALKALOID RING-SYSTEMS [J].

CHAMBERLIN, AR ;

NGUYEN, HD ;

CHUNG, JYL .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (10) :1682-1688

[6] CHEMOENZYMATIC PREPARATION OF TRANS-2,6-DIALKYLPIPERIDINES AND OF OTHER AZACYCLE BUILDING-BLOCKS - TOTAL SYNTHESIS OF (+)-DESOXOPROSOPININE [J].

CIUFOLINI, MA ;

HERMANN, CW ;

WHITMIRE, KH ;

BYRNE, NE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3473-3475

[7] A CONVENIENT SYNTHETIC METHOD FOR AMIDE OXIDATION [J].

HAN, GH ;

MCINTOSH, MC ;

WEINREB, SM .

TETRAHEDRON LETTERS, 1994, 35 (32) :5813-5816

[8] AN ANTIMALARIAL ALKALOID FROM HYDRANGEA .13. THE EFFECTS OF VARIOUS SYNTHETIC QUINAZOLONES AGAINST PLASMODIUM-LOPHURAE IN DUCKS [J].

HEWITT, RI ;

WALLACE, WS ;

GILL, ER ;

WILLIAMS, JH .

AMERICAN JOURNAL OF TROPICAL MEDICINE AND HYGIENE, 1952, 1 (05) :768-772

[9]

KOPEFLI JB, 1950, J AM CHEM SOC, V72, P3323

[10] A FACILE SYNTHESIS OF N-ACYL-2-PYRROLINES [J].

KRAUS, GA ;

NEUENSCHWANDER, K .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (23) :4791-4792