A novel synthesis of tricyclo[5.3.1.0(1,5)]undecanes: Total syntheses of 2-norcedrene and a funebrene analogue

被引:11
作者
Hariprakasha, HK [1 ]
SubbaRao, GSR [1 ]
机构
[1] INDIAN INST SCI,DEPT ORGAN CHEM,BANGALORE 560012,KARNATAKA,INDIA
关键词
D O I
10.1016/S0040-4039(97)01168-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new rearrangement method has been developed for the construction of the tricyclo[5.3.1.0(1.5)]undecane and tricyclo[6.3.1.0(1.6)]dodecane frame works. The key features include the efficient preparations of the alcohols 5, 15 and 19 and their rearrangement to the tricyclic skeleton which led to the synthesis of 2-norcedrene 3 and an analogue of funebrene 13. (C) 1997 Elsevier Science Ltd.
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页码:5343 / 5346
页数:4
相关论文
共 11 条
[1]  
CHEN YJ, 1992, TETRAHEDRON LETT, P1749
[2]  
KAISER R, 1972, TETRAHEDRON LETT, P2009
[3]  
KIRTANY JK, 1973, INDIAN J CHEM, V11, P508
[4]  
KIRTANY K, 1981, INDIAN J CHEM B, V20, P438
[5]  
MOPTL D, 1968, COLLECT CZECH CHEM C, V33, P1939
[6]  
SHANKER PS, 1994, TETRAHEDRON LETT, P5055
[7]   THE STRUCTURE OF CEDRENE [J].
STORK, G ;
BRESLOW, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (13) :3291-3291
[8]   THE TOTAL SYNTHESIS OF CEDROL AND CEDRENE [J].
STORK, G ;
CLARKE, FH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (04) :1072-1073
[9]   A SELECTIVE REDUCTION OF ALPHA,BETA-UNSATURATED KETONES [J].
VONHOLLEBEN, MLA ;
ZUCOLOTTO, M ;
ZINI, CA ;
OLIVEIRA, ER .
TETRAHEDRON, 1994, 50 (04) :973-978
[10]  
Walter P., 1841, LIEBIGS ANN CHEM, V39, P247