AN UNUSUAL REARRANGEMENT OF A CAGE DIKETONE MONOTOSYLHYDRAZONE - A NEW FRAGMENTATION OF THE PCUD SKELETON

被引:5
作者
COXON, JM
FONG, ST
STEEL, PJ
机构
[1] Department of Chemistry, University of Canterbury, Christchurch
关键词
D O I
10.1016/S0040-4039(00)88521-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cage diketone monotosylhydrazone 3 undergoes rearrangement with double alpha-cleavage of the cage skeleton to give a product, 4, which formally corresponds to insertion of cyclopentadiene between the rings of naphthoquinone.
引用
收藏
页码:7479 / 7482
页数:4
相关论文
共 7 条
[1]   PI-FACIAL SELECTIVITY IN DIELS-ALDER REACTIONS OF HEXACYCLO[10.2.1.0(2,11).0(4,9).0(4,14).0(9,13)]PENTADECA-5,7-DIENE-3,10-DIONE [J].
COXON, JM ;
OCONNELL, MJ ;
STEEL, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4726-4732
[2]  
COXON JM, UNPUB J ORG CHEM
[3]  
Marchand A.P., 1989, ADV THEORETICALLY IN, P357
[4]   A STRATEGY FOR THE CONSTRUCTION OF NOVEL TETRACYCLIC LYCOPODIUM ALKALOIDS OF PANICULATINE-TYPE AND MAGELLANINE-TYPE [J].
MEHTA, G ;
REDDY, MS .
TETRAHEDRON LETTERS, 1990, 31 (14) :2039-2042
[5]   A NOVEL, VERSATILE SYNTHETIC APPROACH TO LINEARLY FUSED TRICYCLOPENTANOIDS VIA PHOTO-THERMAL OLEFIN METATHESIS [J].
MEHTA, G ;
SRIKRISHNA, A ;
REDDY, AV ;
NAIR, MS .
TETRAHEDRON, 1981, 37 (25) :4543-4559
[7]   WEDGEBAR-FACIAL STEREOSELECTIVITY IN DIELS-ALDER REACTION OF HEXACYCLO [7.4.2.01,9.03,7.04,14.06,15] PENTADECANE-10,12-DIENE-2,8-DIONE [J].
PANDEY, B ;
ZOPE, UR ;
AYYANGAR, NR .
SYNTHETIC COMMUNICATIONS, 1989, 19 (3-4) :585-596