A TANDEM SYNTHESIS OF (+/-)-EUPHOCOCCININE AND (+/-)-ADALINE

被引：31
作者：
DAVISON, EC
HOLMES, AB
FORBES, IT
机构：
[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND
[2] SMITHKLINE BEECHAM PHARMACEUT,HARLOW CM19 5AW,ESSEX,ENGLAND
来源：
TETRAHEDRON LETTERS | 1995年 / 36卷 / 49期
关键词：
D O I：
10.1016/0040-4039(95)01908-Z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intramolecular hydroxylamine-alkyne cyclisation of the hydroxylamines 8 and 9 afforded six-membered cyclic nitrones which without isolation underwent a tandem intramolecular dipolar cycloaddition to produce the tricyclic isoxazolidines 6 and 7 respectively. These were converted in two steps into the ladybird defence alkaloids (+/-)-euphococcinine 4 and (+/-)-adaline 5.
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页码：9047 / 9050
页数：4
相关论文
共 13 条
[1]  
ALDER K, 1959, LIEBIGS ANN CHEM, V620, P73
[2]   THE DEFENSIVE ALKALOIDS OF CRYPTOLAEMUS-MONTROUZIERI (COLEOPTERA, COCCINELLIDAE) [J].
BROWN, WV ;
MOORE, BP .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (06) :1255-1261
[3]   DEFENSIVE ALKALOID IN BLOOD OF MEXICAN BEAN BEETLE (EPILACHNA-VARIVESTIS) [J].
EISNER, T ;
GOETZ, M ;
ANESHANSLEY, D ;
FERSTANDIGARNOLD, G ;
MEINWALD, J .
EXPERIENTIA, 1986, 42 (02) :204-207
[4]   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 [J].
FOX, ME ;
HOLMES, AB ;
FORBES, IT ;
THOMPSON, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (23) :3379-3395
[5]  
GOSSINGER E, 1980, MONATSH CHEM, V111, P803, DOI 10.1007/BF00899245
[6]   (+)-9-AZA-1-METHYLBICYCLO[3,3,1]NONAN-3-1 A NEW ALKALOID FROM EUPHORBIA ATOTO FORST [J].
HART, NK ;
JOHNS, SR ;
LAMBERTON, JA .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1967, 20 (03) :561-+
[7]   ASYMMETRIC SYNTHESES OF THE LADYBUG ALKALOID ADALINE AND 1-METHYL-9-AZABICYCLO [3.3.1]NONAN-3-ONE [J].
HILL, RK ;
RENBAUM, LA .
TETRAHEDRON, 1982, 38 (13) :1959-1963
[8]   STEREOSELECTIVE SYNTHESIS OF (+/-)-INDOLIZIDINES 167B, 205A, AND 207A - ENANTIOSELECTIVE SYNTHESIS OF (-)-INDOLIZIDINE 209B [J].
HOLMES, AB ;
SMITH, AL ;
WILLIAMS, SF ;
HUGHES, LR ;
LIDERT, Z ;
SWITHENBANK, C .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1393-1405
[9]   OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE [J].
MANCUSO, AJ ;
HUANG, SL ;
SWERN, D .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2480-2482
[10]  
MEDINA DHG, 1983, TETRAHEDRON LETT, V24, P2099
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