A facile method for the solution and solid-phase synthesis of substituted [3.3.1] bicycles

被引:80
作者
Nicolaou, KC
Pfefferkorn, JA
Cao, GQ
Kim, S
Kessabi, J
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[3] Univ Calif San Diego, Dept Biochem & Chem, La Jolla, CA 92093 USA
关键词
D O I
10.1021/ol990791d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Interest in bicyclic natural products from the Guttiferae classification has led to the development of an improved method for the selenium mediated cyclization of alkenyl-substituted beta-dicarbonyls (I) to form a variety of bicyclo[3.3.1]nonan-9-ones (II) both in solution and on solid support.
引用
收藏
页码:807 / 810
页数:4
相关论文
共 34 条
[1]  
Alves TMD, 1999, J NAT PROD, V62, P369, DOI 10.1021/np9803833
[2]   ORGANIC-REACTIONS AT HIGH-PRESSURE - A ROBINSON ANNULATION SEQUENCE INITIATED BY MICHAEL ADDITION OF ACTIVATED CYCLOALKANONES WITH HINDERED ENONES [J].
DAUBEN, WG ;
BUNCE, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) :4642-4648
[3]   Two polyisoprenylated benzophenones from the floral resins of three Clusia species [J].
de Oliveira, CMA ;
Porto, ALM ;
Bittrich, V ;
Marsaioli, AJ .
PHYTOCHEMISTRY, 1999, 50 (06) :1073-1079
[4]   Floral resins of Clusia spp: Chemical composition and biological function [J].
deOliveira, CMA ;
Porto, ALM ;
Bittrich, V ;
Vencato, I ;
Marsaioli, AJ .
TETRAHEDRON LETTERS, 1996, 37 (36) :6427-6430
[5]   ON THE DIRECT FORMATION OF EPISULFONIUM IONS FROM ALKENES - AN APPLICATION TO THE SYNTHESIS OF HIGHER-ORDER CARBOCYCLES VIA EPISULFONIUM ION INITIATED POLYENE CYCLIZATIONS [J].
EDSTROM, ED ;
LIVINGHOUSE, T .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :949-951
[6]   SYNTHESIS OF STABLE ANALOGS OF TXA2 [J].
EVANS, EH ;
HEWSON, AT ;
MARCH, LA ;
NOWELL, IW ;
WADSWORTH, AH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01) :137-149
[7]   INTRAMOLECULAR LEWIS ACID-CATALYZED ALKYLATIONS [J].
EVANS, EH ;
HEWSON, AT ;
WADSWORTH, AH .
SYNTHETIC COMMUNICATIONS, 1985, 15 (03) :243-247
[8]   ENAMINE CHEMISTRY .8. REACTION OF ACRYLOYL CHLORIDE WITH DIENAMINES [J].
FIRRELL, NF ;
HICKMOTT, PW ;
HOPKINS, BJ .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (10) :1477-&
[9]   BRIDGED AMINOTETRALINS AS NOVEL POTENT ANALGESIC SUBSTANCES [J].
FREED, ME ;
POTOSKI, JR ;
FREED, EH ;
CONKLIN, GL ;
MALIS, JL .
JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (06) :595-599
[10]  
Fukuyama Y, 1997, CHEM PHARM BULL, V45, P947