An efficient approach to bridged-bicyclic rings via intramolecular diazo ketone insertion

被引:6
作者
Chen, L [1 ]
Zhang, XQ [1 ]
Schultz, A [1 ]
机构
[1] Rensselaer Polytech Inst, Dept Chem, Troy, NY 12180 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(02)00878-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A regioselective intramolecular diazo ketone insertion reaction of chiral cyclohexenones is described. The methodology shows potential utility in the syntheses of bicyclo[4.2.1]nonan-9-one, bicyclo[4.3.1]decan-10-one and cyclooctanoid rings. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4711 / 4715
页数:5
相关论文
共 20 条
[1]   ROSEADIONE, A DITERPENE KETONE FROM HYPOESTES-ROSEA [J].
ADESOMOJU, AA ;
OKOGUN, JI ;
CAVA, MP ;
CARROLL, PJ .
PHYTOCHEMISTRY, 1983, 22 (11) :2535-2536
[2]  
Bailey D.M., 1963, J ORG CHEM, V28, P610
[3]   KALMANOL, A PHARMACOLOGICALLY ACTIVE DITERPENOID WITH A NEW RING SKELETON FROM KALMIA-ANGUSTIFOLIA L [J].
BURKE, JW ;
DOSKOTCH, RW ;
NI, CZ ;
CLARDY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (15) :5831-5833
[4]  
COREY EJ, 1975, SYNTHESIS-STUTTGART, P590
[5]  
Dabrah TT, 1997, J ANTIBIOT, V50, P1
[6]   VARIECOLIN, A SESTERTERPENOID OF NOVEL SKELETON FROM ASPERGILLUS-VARIECOLOR MF138 [J].
HENSENS, OD ;
ZINK, D ;
WILLIAMSON, JM ;
LOTTI, VJ ;
CHANG, RSL ;
GOETZ, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) :3399-3403
[7]   THE USE OF OMEGA-IODOAZIDES AS PRIMARY PROTECTED ELECTROPHILIC REAGENTS - ALKYLATION OF SOME CARBANIONS DERIVED FROM ACTIVE METHYLENE-COMPOUNDS AND N,N-DIMETHYLHYDRAZONES [J].
KHOUKHI, M ;
VAULTIER, M ;
CARRIE, R .
TETRAHEDRON LETTERS, 1986, 27 (09) :1031-1034
[8]  
MCCLOSKEY PJ, 1987, HETEROCYCLES, V25, P437
[9]   Progress in the construction of cyclooctanoid systems: New approaches and applications to natural product syntheses [J].
Mehta, G ;
Singh, V .
CHEMICAL REVIEWS, 1999, 99 (03) :881-930
[10]  
Nicolaou KC, 2000, ANGEW CHEM INT EDIT, V39, P1829, DOI 10.1002/(SICI)1521-3773(20000515)39:10<1829::AID-ANIE1829>3.0.CO