A 4+3 cycloaddition approach to the spatane ring system

被引:14
作者
Harmata, M [1 ]
Rashatasakhon, P [1 ]
机构
[1] Univ Missouri, Dept Chem, Columbia, MO 65211 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(01)01012-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The adduct of dichloroketene and cyclopentene was converted to a tricyclo[5.3.0.0(2.6)]decane ring system using a 4+3 cycloaddition reaction followed by a quasi-Favorskii rearrangement as the key steps. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5593 / 5595
页数:3
相关论文
共 28 条
[1]  
[Anonymous], 1997, Organic Reactions
[2]  
[Anonymous], 1997, Advances in Cycloaddition
[3]  
Cha JK, 1998, CURR ORG CHEM, V2, P217
[4]  
Claus R. E., 1986, ORG SYNTH, V64, P150
[5]   PHOTOCHEMISTRY OF 2,7-CYCLOOCTADIENONE [J].
CRANDALL, JK ;
HASELTIN.RP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (22) :6251-&
[6]   TOTAL SYNTHESIS OF (13Z)-SPATA-13(15),17-DIENE, AND THE FORMAL SYNTHESIS OF SPATOL [J].
DAUBEN, WG ;
KOWALCZYK, BA .
TETRAHEDRON LETTERS, 1990, 31 (05) :635-638
[7]   SYNTHESIS OF SUBSTITUTED CIS-BICYCLO[3.3.0]OCTANE-1-CARBONYL DERIVATIVES BY STEREOSPECIFIC REARRANGEMENT OF 1-CHLORO-9-HYDROXYBICYCLO-[3.3.1]NONANES [J].
GAMBACORTA, A ;
TURCHETTA, S ;
BOVICELLI, P ;
BOTTA, M .
TETRAHEDRON, 1991, 47 (43) :9097-9102
[8]   ISOLATION AND STRUCTURE OF SPATOL, A POTENT INHIBITOR OF CELL REPLICATION FROM THE BROWN SEAWEED SPATOGLOSSUM-SCHMITTII [J].
GERWICK, WH ;
FENICAL, W ;
VANENGEN, D ;
CLARDY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (27) :7991-7993
[9]  
GERWICK WH, 1983, J ORG CHEM, V48, P3325, DOI 10.1021/jo00167a033
[10]   SPATANE DITERPENOIDS FROM THE TROPICAL MARINE ALGA STOECHOSPERMUM-MARGINATUM (DICTYOTACEAE) [J].
GERWICK, WH ;
FENICAL, W ;
SULTANBAWA, MUS .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (11) :2233-2241