REGIOSELECTIVE NUCLEOPHILIC RING-OPENING OF OXABICYCLIC COMPOUNDS

被引:23
作者
LAUTENS, M
CHIU, P
机构
[1] Department of Chemistry University of Toronto, Toronto
关键词
D O I
10.1016/0040-4039(93)89008-E
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ring opening of unsymmetrical oxabicyclic compounds was found to be highly regioselective, giving rise to products from the attack of the nucleophile distal to the bridgehead substituent. Ozonolysis furnished acyclic chains with up to five stereocenters and differentiated ends.
引用
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页码:773 / 776
页数:4
相关论文
共 12 条
[1]   STRAIN-DIRECTED BRIDGE CLEAVAGE OF (PHENYLSULFONYL)-7-OXABICYCLO[2.2.1]HEPTANE DERIVATIVES - APPLICATION TO THE TOTAL SYNTHESIS OF CARBA-ALPHA-DL-GLUCOPYRANOSE [J].
ACENA, JL ;
ARJONA, O ;
DELAPRADILLA, RF ;
PLUMET, J ;
VISO, A .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1945-1946
[2]   REGIOSPECIFIC AND STEREOSPECIFIC SYNTHESIS OF SUBSTITUTED CYCLOHEXENEDIOLS FROM 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-OLS AND ORGANO-LITHIUM REAGENTS [J].
ARJONA, O ;
DELAPRADILLA, RF ;
GARCIA, E ;
MARTINDOMENECH, A ;
PLUMET, J .
TETRAHEDRON LETTERS, 1989, 30 (46) :6437-6440
[3]  
BELTER RK, UNPUB
[4]   AN EFFICIENT SYNTHESIS OF 1,3-CYCLOHEXADIENES FROM OXABICYCLO[2.2.1.]HEPTENES VIA TANDEM RING-OPENING PETERSON ELIMINATION-REACTIONS [J].
LAUTENS, M ;
MA, SH ;
BELTER, RK ;
CHIU, P ;
LESCHZINER, A .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4065-4066
[5]   THE EFFECT OF REMOTE OXYGENS ON THE RING-OPENING REACTIONS OF OXABICYCLIC COMPOUNDS WITH ORGANOLITHIUM REAGENTS - SYNTHESIS OF THE C21-C27 SEGMENT OF RIFAMYCIN-S [J].
LAUTENS, M ;
BELTER, RK .
TETRAHEDRON LETTERS, 1992, 33 (19) :2617-2620
[6]   RING-OPENING REACTIONS OF AN OXABICYCLIC COMPOUND WITH CUPRATES [J].
LAUTENS, M ;
DIFELICE, C ;
HUBOUX, A .
TETRAHEDRON LETTERS, 1989, 30 (49) :6817-6820
[7]   THE REDUCTIVE RING-OPENING OF OXABICYCLIC COMPOUNDS [J].
LAUTENS, M ;
CHIU, P .
TETRAHEDRON LETTERS, 1991, 32 (37) :4827-4830
[8]   OPENING OF OXABICYCLO[3.2.1]OCTENES WITH ORGANOLITHIUM REAGENTS - A ROUTE TO CYCLIC AND ACYCLIC COMPOUNDS WITH HIGH STEREOCONTROL [J].
LAUTENS, M ;
ABDELAZIZ, AS ;
LOUGH, A .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) :5305-5306
[9]   PREPARATION OF CYCLOHEXENYL DERIVATIVES BY THE RING-OPENING REACTIONS OF OXABICYCLO[2.2.1] COMPOUNDS WITH CUPRATES [J].
LAUTENS, M ;
SMITH, AC ;
ABDELAZIZ, AS ;
HUBOUX, AH .
TETRAHEDRON LETTERS, 1990, 31 (23) :3253-3256
[10]   A GENERAL-APPROACH TO THE SYNTHESIS OF C-8-OXYGENATED GUAIANOLIDES [J].
RIGBY, JH ;
WILSON, JAZ .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (01) :34-44