Cleavage of the oxygen bridge in 8-oxabicyclo [3.2.1]octanes by reductive elimination

被引:10
作者
Föhlisch, B [1 ]
Kreiselmeier, G [1 ]
机构
[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
关键词
cycloadditions; halohydrins; haloketones; cycloheptenes; oxyallyl intermediates; furans; diols;
D O I
10.1016/S0040-4020(01)01051-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several 2(4)-bromo- or chloro-8-oxabicyclo[3.2.1]oct-6-en-3-ones (2), available by [4+3] cycloaddition of monohalogenooxyallyl intermediates with furans, were reduced to halogenated 8-oxabicyclo[3.2.1]oct-6-en-3endo-ols (6) and saturated analogues (7). Cycloheptene-1,3trans-diols (8,11) were formed preferentially by reductive elimination. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:10077 / 10088
页数:12
相关论文
共 49 条
[1]  
[Anonymous], 1997, Organic Reactions
[2]   SYNTHESIS OF A STABLE ANALOG OF THROMBOXANE-A1 (+/-)-9A-HOMO-(11,12)-DEOXA-(11,12)-METHYLENE THROMBOXANE-A1 [J].
ANSELL, MF ;
CATON, MPL ;
MASON, JS .
TETRAHEDRON LETTERS, 1981, 22 (12) :1141-1142
[3]   THE SYNTHESIS OF (+/-)-10A-HOMO-11A-CARBATHROMBOXANE-A1, A STABLE THROMBOXANE A-ANALOG [J].
ANSELL, MF ;
MASON, JS ;
CATON, MPL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :1061-1068
[4]   Synthesis of key intermediates for a concise and convergent approach to the marine natural product eleutherobin [J].
Baron, A ;
Caprio, V ;
Mann, J .
TETRAHEDRON LETTERS, 1999, 40 (52) :9321-9324
[5]  
Beck H, 1999, EUR J ORG CHEM, V1999, P2991
[6]   TOTAL SYNTHESIS OF (+/-)-BETA-BULNESENE VIA INTRAMOLECULAR CYCLO-ADDITION OF A 2-SUBSTITUTED 3-OXIDOPYRYLIUM [J].
BROMIDGE, SM ;
SAMMES, PG ;
STREET, LJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (08) :1725-1730
[7]  
Chiu P, 1997, TOP CURR CHEM, V190, P1
[8]   Diastereocontrol of [4+3] cyclic oxyallyl cycloadditions by alkoxy substituents [J].
Cho, SY ;
Lee, JC ;
Cha, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3394-3395
[9]   CONSTRUCTION OF 8-OXABICYCLO[5.3.0]DECA-2,9-DIONES - AN APPROACH TO THE PSEUDOGUAIANOLIDES [J].
CUMMINS, WJ ;
DREW, MGB ;
MANN, J ;
MARKSON, AJ .
TETRAHEDRON, 1988, 44 (16) :5151-5160
[10]   2-OXO-1,3-ALKADIYL DIRADICALS . DEHALOGENATION OF ALPHA,ALPHA'-DIHALO KETONES WITH POTASSIUM VAPOR [J].
DOERR, RG ;
SKELL, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (18) :4684-&