Convenient annulation of bicyclo[6.3.0]undecanes

被引:5
作者
Lee, K [1 ]
Cha, JK [1 ]
机构
[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(01)01184-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile, albeit nonstereoselective, method for the construction of a bicyclo[6.3.0]undecane skeleton has been developed by sequential application of the Suarez cleavage and 5-exo radical cyclization on the readily available [4+3] cycloadducts of cyclic oxyallyls. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6019 / 6021
页数:3
相关论文
共 22 条
[1]  
[Anonymous], UNPUB
[2]   TANDEM FREE-RADICAL RING EXPANSION AND 5-EXO-DIG 5-HEXYNYL RADICAL CYCLIZATION - A USEFUL APPROACH TO FUSED BICYCLIC CARBOCYCLES [J].
BOGER, DL ;
MATHVINK, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (20) :5442-5444
[3]   IRON(III) MEDIATED TRANSFORMATIONS OF CYCLOPROPYLTRIMETHYLSILYL ETHERS .1. FREE-RADICAL TANDEM RING EXPANSION-CYCLIZATION REACTIONS FOR THE RAPID CONSTRUCTION OF [N30] BICYCLIC RING-SYSTEMS [J].
BOOKERMILBURN, KI ;
THOMPSON, DF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (18) :2315-2321
[4]  
BOOKERMILBURN KI, 1992, SYNLETT, P809
[5]  
Curran D. P., 1996, STEREOCHEMISTRY RADI
[6]   FRAGMENTATION OF CARBOHYDRATE ANOMERIC ALKOXY RADICALS - TANDEM BETA-FRAGMENTATION-CYCLIZATION OF ALCOHOLS [J].
DEARMAS, P ;
FRANCISCO, CG ;
SUAREZ, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (19) :8865-8866
[7]   SYNTHESIS OF MEDIUM-SIZED LACTONES - IODOSOBENZENE DIACETATE AN EFFICIENT REAGENT FOR BETA-FRAGMENTATION OF ALKOXY RADICALS [J].
FREIRE, R ;
MARRERO, JJ ;
RODRIGUEZ, MS ;
SUAREZ, E .
TETRAHEDRON LETTERS, 1986, 27 (03) :383-386
[8]   SYNTHESIS OF MEDIUM-SIZED BICYCLIC COMPOUNDS BY INTRAMOLECULAR CYCLIZATION OF CYCLIC BETA-KETO RADICALS GENERATED FROM CYCLOPROPANOLS USING MANGANESE(III) TRIS(2-PYRIDINECARBOXYLATE) [J].
IWASAWA, N ;
FUNAHASHI, M ;
HAYAKAWA, S ;
NARASAKA, K .
CHEMISTRY LETTERS, 1993, (03) :545-548
[9]   GENERATION OF BETA-CARBONYL RADICALS FROM CYCLOPROPANOL DERIVATIVES BY THE OXIDATION WITH MANGANESE(III) 2-PYRIDINECARBOXYLATE AND THEIR REACTIONS WITH ELECTRON-RICH AND ELECTRON-DEFICIENT OLEFINS [J].
IWASAWA, N ;
HAYAKAWA, S ;
FUNAHASHI, M ;
ISOBE, K ;
NARASAKA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (03) :819-827
[10]   [4+3]CYCLOADDITIONS OF CYCLIC OXYALLYLS AND CYCLIC 1,3-DIENES [J].
JIN, SJ ;
CHOI, JR ;
OH, JH ;
LEE, DH ;
CHA, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :10914-10921