The Claisen rearrangement approach to fused bicyclic medium-ring oxacycles

被引:16
作者
Burton, Jonathan W. [1 ,2 ]
Anderson, Edward A. [1 ]
O'Sullivan, Paul T. [1 ]
Collins, Ian [3 ]
Davies, John E. [1 ]
Bond, Andrew D. [1 ]
Feeder, Neil [1 ]
Holmes, Andrew B. [1 ,4 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
[2] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England
[3] Inst Canc Res, Sutton SM2 5NG, Surrey, England
[4] Univ Melbourne, Inst Bio21, Sch Chem, Melbourne, Vic 3010, Australia
关键词
D O I
10.1039/b715354f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of five fused-bicyclic medium-ring lactones carrying identical ring-fusion to that in the polyether toxins is described using an enolate hydroxylation, intramolecular hydrosilation, Claisen rearrangement sequence.
引用
收藏
页码:693 / 702
页数:10
相关论文
共 76 条
[1]   USEFUL DESIGNS IN THE SYNTHESIS OF TRANS-FUSED POLYETHER TOXINS [J].
ALVAREZ, E ;
CANDENAS, ML ;
PEREZ, R ;
RAVELO, JL ;
MARTIN, JD .
CHEMICAL REVIEWS, 1995, 95 (06) :1953-1980
[2]   Synthesis of medium-ring lactones via tandem methylenation/Claisen rearrangement of cyclic carbonates [J].
Anderson, EA ;
Davidson, JEP ;
Harrison, JR ;
O'Sullivan, PT ;
Burton, JW ;
Collins, I ;
Holmes, AB .
TETRAHEDRON, 2002, 58 (10) :1943-1971
[3]  
ANH NT, 1977, NOUV J CHIM, V1, P61
[4]   CHORISMATE MUTASE INHIBITORS - SYNTHESIS AND EVALUATION OF SOME POTENTIAL TRANSITION-STATE ANALOGS [J].
BARTLETT, PA ;
NAKAGAWA, Y ;
JOHNSON, CR ;
REICH, SH ;
LUIS, A .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3195-3210
[5]   ASYMMETRIC CATALYSIS - MECHANISM OF ASYMMETRIC CATALYTIC INTRAMOLECULAR HYDROSILATION [J].
BERGENS, SH ;
NOHEDA, P ;
WHELAN, J ;
BOSNICH, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) :2128-2135
[6]   ASYMMETRIC CATALYSIS - PRODUCTION OF CHIRAL DIOLS BY ENANTIOSELECTIVE CATALYTIC INTRAMOLECULAR HYDROSILATION OF OLEFINS [J].
BERGENS, SH ;
NOHEDA, P ;
WHELAN, J ;
BOSNICH, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) :2121-2128
[7]  
BREVETOXIN A, 1998, NATURE, V392, P264
[8]  
BREVETOXIN B, 1995, J AM CHEM SOC, V117, P10227
[9]   A SAFE AND EFFICIENT METHOD FOR CONVERSION OF 1,2-DIOLS AND 1,3-DIOLS TO CYCLIC CARBONATES UTILIZING TRIPHOSGENE [J].
BURK, RM ;
ROOF, MB .
TETRAHEDRON LETTERS, 1993, 34 (03) :395-398
[10]   Synthesis of medium ring ethers .5. The synthesis of (+)-laurencin [J].
Burton, JW ;
Clark, JS ;
Derrer, S ;
Stork, TC ;
Bendall, JG ;
Holmes, AB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (32) :7483-7498