A SYNTHESIS OF (+/-)-7-METHOXYCARBONYL-2-(3-METHOXYPHENYLMETHYLIDENE)-8-METHYL-3,8-DIAZABICYCLO[3.2.1]OCTAN-4-ONE (1B) USING DIPOLAR CYCLOADDITION TO A 3-OXIDOPYRAZINIUM

被引:27
作者
ALLWAY, PA [1 ]
SUTHERLAND, JK [1 ]
JOULE, JA [1 ]
机构
[1] UNIV MANCHESTER,DEPT CHEM,MANCHESTER M13 9PL,LANCS,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)97732-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 3-methoxybenzyl-substituted 3,8-diazabicyclo[3.2.1]octane 1b, was prepared in 8 steps from 3-methoxybenzaldehyde, utilising, as the key step, the dipolar cycloaddition of methyl acrylate to a 5-benzyl-substituted 3-oxidopyrazinium, 5. © 1990.
引用
收藏
页码:4781 / 4782
页数:2
相关论文
共 11 条
[1]   HARD ACID AND SOFT NUCLEOPHILE SYSTEM - NEW EFFICIENT METHOD FOR REMOVAL OF BENZYL PROTECTING GROUP [J].
FUJI, K ;
ICHIKAWA, K ;
NODE, M ;
FUJITA, E .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) :1661-1664
[2]   COMPLEX PYRROLIDINES VIA A TANDEM MICHAEL REACTION/1,3-DIPOLAR CYCLOADDITION SEQUENCE - A NOVEL METHOD FOR THE GENERATION OF UNSYMMETRICAL AZOMETHINE YLIDES [J].
GARNER, P ;
ARYA, F ;
HO, WB .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :412-414
[3]   AN ASYMMETRIC APPROACH TO NAPHTHYRIDINOMYCIN AND QUINOCARCIN VIA A REMARKABLY SELECTIVE INTRAMOLECULAR 1,3-DIPOLAR CYCLO-ADDITION REACTION [J].
GARNER, P ;
SUNITHA, K ;
HO, WB ;
YOUNGS, WJ ;
KENNEDY, VO ;
DJEBLI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (09) :2041-2042
[4]   AN APPROACH TO THE 3,8-DIAZABICYCLO[3.2.1]OCTANE MOIETY OF NAPHTHYRIDINOMYCIN AND QUINOCARCIN VIA 1,3-DIPOLAR CYCLO-ADDITION OF PHOTOCHEMICALLY GENERATED AZOMETHINE YLIDES [J].
GARNER, P ;
SUNITHA, K ;
SHANTHILAL, T .
TETRAHEDRON LETTERS, 1988, 29 (29) :3525-3528
[5]   X-RAY DETERMINATION OF THE MOLECULAR-STRUCTURE OF THE NOVEL ANTIBIOTIC DC-52-D, 6-HYDROXYMETHYL-3,12-IMINO-7-METHOXY-13-METHYL-1,2,3,4-TETRAHYDROAZEPINO[1,2-B]ISOQUINOLINE-1-CARBOXYLIC ACID [J].
HIRAYAMA, N ;
SHIRAHATA, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1983, (11) :1705-1708
[6]   1,3-DIPOLAR CYCLOADDITIONS TO OXIDOPYRAZINIUMS [J].
KISS, M ;
RUSSELLMAYNARD, J ;
JOULE, JA .
TETRAHEDRON LETTERS, 1987, 28 (19) :2187-2190
[7]   SYNTHESIS OF AN ADVANCED QUINOCARCIN INTERMEDIATE FROM L-GLUTAMIC ACID [J].
LESSEN, TA ;
DEMKO, DM ;
WEINREB, SM .
TETRAHEDRON LETTERS, 1990, 31 (15) :2105-2108
[8]   SYNTHESIS OF PHENYL-SUBSTITUTED 1-AMINOTETRALINES [J].
SARGES, R .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (09) :1216-1224
[9]   DC-52, A NOVEL ANTI-TUMOR ANTIBIOTIC .2. ISOLATION, PHYSICOCHEMICAL CHARACTERISTICS AND STRUCTURE DETERMINATION [J].
TAKAHASHI, K ;
TOMITA, F .
JOURNAL OF ANTIBIOTICS, 1983, 36 (05) :468-470
[10]   DC-52, A NOVEL ANTI-TUMOR ANTIBIOTIC .1. TAXONOMY, FERMENTATION AND BIOLOGICAL-ACTIVITY [J].
TOMITA, F ;
TAKAHASHI, K ;
SHIMIZU, K .
JOURNAL OF ANTIBIOTICS, 1983, 36 (05) :463-467