N-ALKENYL NITRONE DIPOLAR CYCLOADDITION ROUTES TO PIPERIDINES AND INDOLIZIDINES .7. HYDROXYLAMINE ALKYNE CYCLIZATIONS - FORMATION OF CYCLIC NITRONES AND APPLICATION TO THE SYNTHESIS OF THE PROPOSED STRUCTURE FOR (+/-)-ACACIALACTAM

被引:29
作者
FOX, ME
HOLMES, AB
FORBES, IT
THOMPSON, M
机构
[1] UNIV CAMBRIDGE, CHEM LAB, CAMBRIDGE CB2 1EW, ENGLAND
[2] SMITHKLINE BEECHAM PHARMACEUT, MED RES CTR, HARLOW CM19 5AD, ESSEX, ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 23期
关键词
D O I
10.1039/p19940003379
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cyclisation of the alkynylhydroxylamines 2, 13, 14, 19, 27, 34, 39, 46 and 47 to give five-, six- and seven-membered cyclic nitrones is described. A concerted intramolecular ene-like pathway is proposed for the addition of the N-O-H group across the triple bond. Using the nitrone 48 as the starting material, the seven-membered lactam structure 49 proposed for the natural product acacialactam was prepared and was found to be incorrect.
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页码:3379 / 3395
页数:17
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