ENANTIOPURE N-ACYLDIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - AN ASYMMETRIC-SYNTHESIS OF SOLENOPSIN-A

被引：41

作者：

COMINS, DL

BENJELLOUN, NR

机构：

[1] Department of Chemistry North Carolina State University, Raleigh

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 06期

关键词：

D O I：

10.1016/S0040-4039(00)75974-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The trans-piperidine alkaloid, (-)-solenopsin A, was prepared in seven steps form readily available 4-methoxy-3-(triisopropylsilyl)pyridine in 43% overall yield.

引用

页码：829 / 832

页数：4

共 36 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] ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS FROM DIPOLE-STABILIZED CARBANIONS - THE TERT-BOC GROUP AS AN ACTIVATOR FOR ALPHA'-LITHIATION OF CARBAMATES [J].

BEAK, P ;

LEE, WK .

TETRAHEDRON LETTERS, 1989, 30 (10) :1197-1200

[3] 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

[4] ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - SYNTHESES OF DIASTEREOISOMERS FROM THE BOC PIPERIDINES [J].

BEAK, P ;

LEE, WK .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2578-2580

[5]

BLUM MS, 1985, ACS SYM SER, V276, P393

[6] SYNTHESIS OF TRANS-2,6-DIALKYLPIPERIDINES BY INTRAMOLECULAR AMIDOMERCURATION [J].

CARRUTHERS, W ;

WILLIAMS, MJ ;

COX, MT .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (18) :1235-1236

[7] AN EFFICIENT ASYMMETRIC-SYNTHESIS OF 1-ACYL-2-ALKYL-1,2-DIHYDROPYRIDINES [J].

COMINS, DL ;

HONG, H ;

SALVADOR, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (26) :7197-7199

[8] CHIRAL DIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - ASYMMETRIC-SYNTHESIS OF (+)-ELAEOKANINE-A AND (+)-ELAEOKANINE-C [J].

COMINS, DL ;

HONG, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) :6672-6673

[9] ASYMMETRIC-SYNTHESIS OF 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES BY ADDITION OF GRIGNARD-REAGENTS TO CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS [J].

COMINS, DL ;

GOEHRING, RR ;

JOSEPH, SP ;

OCONNOR, S .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2574-2576

[10] STEREOCONTROLLED PREPARATION OF CIS-2,6-DIALKYLPIPERIDINE AND TRANS-2,6-DIALKYLPIPERIDINE VIA 1-ACYLDIHYDROPYRIDINE INTERMEDIATES - SYNTHESIS OF (+/-)-SOLENOPSIN-A AND (+/-)-DIHYDROPINIDINE [J].

COMINS, DL ;

WEGLARZ, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2506-2512

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