TRANSANNULAR DIELS-ALDER REACTION ON MACROCYCLES - A GENERAL STRATEGY FOR THE SYNTHESIS OF POLYCYCLIC COMPOUNDS

被引:56
作者
DESLONGCHAMPS, P
机构
[1] Laboratoire de Synthese Organique, Departement de Chimie, Universite de Sherbrooke, Sherbrooke, QC
关键词
D O I
10.1351/pac199264121831
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Various aspects of the transannular Diels-Alder reaction are examined in order to eventually develop a general method for the synthesis of a large variety of polycyclic compounds related to the diterpenes, triterpenes and steroids. Emphasis is made on the control of the relative and absolute configuration of the polycyclic products. Preliminary work towards the synthesis of some specific target natural products is also presented.
引用
收藏
页码:1831 / 1847
页数:17
相关论文
共 40 条
[1]   SYNTHESIS AND TRANS-ANNULAR DIELS-ALDER REACTION OF A TRANS-CIS-CIS 13-MEMBERED MACROCYCLIC TRIENONE [J].
BAETTIG, K ;
MARINIER, A ;
PITTELOUD, R ;
DESLONGCHAMPS, P .
TETRAHEDRON LETTERS, 1987, 28 (44) :5253-5254
[2]   SYNTHESIS AND TRANS-ANNULAR DIELS-ALDER REACTION OF A CIS-TRANS-TRANS 13-MEMBERED MACROCYCLIC TRIENONE [J].
BAETTIG, K ;
DALLAIRE, C ;
PITTELOUD, R ;
DESLONGCHAMPS, P .
TETRAHEDRON LETTERS, 1987, 28 (44) :5249-5252
[3]  
BAETTIG K, UNPUB
[4]   TOTAL SYNTHESIS OF RYANODOL [J].
BELANGER, A ;
BERNEY, DJF ;
BORSCHBERG, HJ ;
BROUSSEAU, R ;
DOUTHEAU, A ;
DURAND, R ;
KATAYAMA, H ;
LAPALME, R ;
LETURC, DM ;
LIAO, CC ;
MACLACHLAN, FN ;
MAFFRAND, JP ;
MARAZZA, F ;
MARTINO, R ;
MOREAU, C ;
SAINTLAURENT, L ;
SAINTONGE, R ;
SOUCY, P ;
RUEST, L ;
DESLONGCHAMPS, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (24) :3348-3354
[5]  
BERTHIAUME S, 1989, THESIS U SHERBROOKE
[6]   SYNTHESIS AND TRANS-ANNULAR DIELS-ALDER REACTION OF A 13-MEMBERED MACROCYCLIC TRIENE HAVING A TETRASUBSTITUTED ENOL ETHER AS A DIENOPHILE [J].
BERUBE, G ;
DESLONGCHAMPS, P .
TETRAHEDRON LETTERS, 1987, 28 (44) :5255-5258
[7]   SYNTHESIS AND TRANSANNULAR DIELS-ALDER REACTION OF A 13-MEMBERED MACROCYCLIC TRIENE HAVING A TETRASUBSTITUTED ENOL ETHER AS DIENOPHILE [J].
BERUBE, G ;
DESLONGCHAMPS, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (03) :404-411
[8]   STUDY ON THE INFLUENCE OF UNSATURATIONS ON THE FORMATION OF C-11, C-12, C-13 AND C-14 MEMBERED RINGS [J].
BRILLON, D ;
DESLONGCHAMPS, P .
TETRAHEDRON LETTERS, 1986, 27 (10) :1131-1134
[9]   SYNTHESIS OF 11-MEMBERED AND 12-MEMBERED RINGS BY A DIRECT CYCLIZATION METHOD [J].
BRILLON, D ;
DESLONGCHAMPS, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (01) :43-55
[10]   SYNTHESIS OF 13-MEMBERED AND 14-MEMBERED RINGS BY A DIRECT CYCLIZATION METHOD [J].
BRILLON, D ;
DESLONGCHAMPS, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (01) :56-68