Synthetic studies on the ceveratrum alkaloid skeleton

被引：8

作者：

Jones, K ^{[1
]}

Newton, RF ^{[1
]}

Yarnold, CJ ^{[1
]}

机构：

[1] GLAXO WELLCOME,STEVENAGE SG1 2NY,HERTS,ENGLAND

来源：

TETRAHEDRON | 1996年 / 52卷 / 11期

关键词：

D O I：

10.1016/S0040-4020(96)00074-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-(2-Cyclohexenyl-1-carbonyl)-piperidine-2-carboxaldehyde oxime (23) was prepared in 5 steps from pyridine-2-carboxaldehyde. Oxidation with NaOCl afforded the corresponding nitrile oxide which cyclized to give a 1:1 ratio of diastereomers 2a alpha,3,4,5,5a alpha,9,10,11 alpha,beta,11c alpha-decahydro-6H,8H-[1,2] benzisoxazolo [3,4-ab] quinolizin-6-one (24A) and 2a alpha,3,4,5,5a alpha,9,10,11a alpha,11c alpha-decahydro-6H,8H-[1,2] benzisoxazolo [3,4-ab] quinolizin-6-one (24B) in a best yield of 30%.

引用

页码：4133 / 4140

页数：8

共 29 条

[21] PAYNE GB, 1977, Patent No. 4025634
[22] Poethke W, 1937, ARCH PHARM, V275, P571
[23] QUIMPERE M, 1992, SYNTHESIS-STUTTGART, P132
[24] NITROENAMINES - PREPARATION, STRUCTURE AND SYNTHETIC POTENTIAL
RAJAPPA, S
[J]. TETRAHEDRON, 1981, 37 (08) : 1453 - 1480
[25] SILVERSTEIN RM, 1991, SPECTROMETRIC IDENTI, P197
[26] STORK G, 1989, NEW ASPECTS ORGANIC, V1, P3
[27] Teeter H.M., 1963, ORG SYNTH, V4, P125
[28] Tomko J., 1973, ALKALOIDS CHEM PHYSL, V14, P1
[29] Torssell K.B. G., 1988, NITRILE OXIDES NITRO

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