A new asymmetric entry to 2-substituted piperidines. A concise synthesis of (+)-coniine, (-)-pelletierine, (+)-delta-coniceine, and (+)-epidihydropinidine

被引：68

作者：

Takahata, H ^{[1
]}

Kubota, M ^{[1
]}

Takahashi, S ^{[1
]}

Momose, T ^{[1
]}

机构：

[1] TOYAMA MED & PHARMACEUT UNIV,FAC PHARMACEUT SCI,TOYAMA 93001,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 10期

关键词：

D O I：

10.1016/0957-4166(96)00395-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new asymmetric route to 2-substituted piperidines involving the Sharpless asymmetric dihydroxylation (AD) of 5-hexenylazide 1 and an intramolecular aminocyclization as crucial steps and its application to the asymmetric synthesis of four piperidine alkaloids, (+)-coniine 2, (-)-pelletierine 3, (+)-delta-coniceine 4, and (+)-epidihydropinidine 5 is presented. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

页码：3047 / 3054

页数：8

共 29 条

[1] CONVERSION OF N-ACYL-2,3-DIHYDRO-4-PYRIDONES TO 4-CHLORO-1,2-DIHYDROPYRIDINES USING THE VILSMEIER REAGENT [J].

ALAWAR, RS ;

JOSEPH, SP ;

COMINS, DL .

TETRAHEDRON LETTERS, 1992, 33 (50) :7635-7638

[2] CHIRAL PRECURSORS FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE PIPERIDINES - TOTAL SYNTHESIS OF (R)-(-)-CONIINE [J].

AMAT, M ;

LLOR, N ;

BOSCH, J .

TETRAHEDRON LETTERS, 1994, 35 (14) :2223-2226

[3] ENANTIOSELECTIVE SYNTHESIS OF (+)-INDOLIZIDINE, (+)-LABURNINE AND (+)-ELAEOKANINES A AND C USING THE DIELS-ALDER REACTION OF ALPHA-(2-EXO-HYDROXY-10-BORNYLSULFINYL)MALEIMIDE [J].

ARAI, Y ;

KONTANI, T ;

KOIZUMI, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (01) :15-23

[4] ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - SYNTHESES OF DIASTEREOISOMERS FROM BOC DERIVATIVES OF CYCLIC AMINES [J].

BEAK, P ;

LEE, WK .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1109-1117

[5] A new ligand class for the asymmetric dihydroxylation of olefins [J].

Becker, H ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :448-451

[6] IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS [J].

CRISPINO, GA ;

JEONG, KS ;

KOLB, HC ;

WANG, ZM ;

XU, DQ ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3785-3786

[7]

ENDERS D, 1993, LIEBIGS ANN CHEM, P173

[8]

Fodor G. B., 1986, Alkaloids: Chemical and Biological Properties, V3, P1

[9] NEW HIGHLY ENANTIOSELECTIVE SYNTHESIS OF 6-ALKYLPIPERIDIN-2-ONES AND 2-SUBSTITUTED PIPERIDINES [J].

FREVILLE, S ;

CELERIER, JP ;

THUY, VM ;

LHOMMET, G .

TETRAHEDRON-ASYMMETRY, 1995, 6 (11) :2651-2654

[10] *UBER DIE RACEMISIERUNG DES ISOPELLETIERINS UND METHYLISOPELLETIERINS [J].

GALINOVSKY, F ;

BIANCHETTI, G ;

VOGL, O .

MONATSHEFTE FUR CHEMIE, 1953, 84 (06) :1221-1227

← 1 2 3 →