STEREOCONTROLLED CONSTRUCTION OF A.B.C.[6.6.6] TRICYCLE VIA TRANSANNULAR DIELS-ALDER REACTION OF 14-MEMBERED TRIENE MACROCYCLE

被引:6
作者
CANTIN, M [1 ]
XU, YC [1 ]
DESLONGCHAMPS, P [1 ]
机构
[1] UNIV SHERBROOKE,FAC SCI,DEPT CHIM,SYNTHESE ORGAN LAB,SHERBROOKE J1K 2R1,QUEBEC,CANADA
来源
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1990年 / 68卷 / 12期
关键词
STEREOCONTROLLED SYNTHESIS; MACROCYCLE; TRICYCLIC COMPOUND; TRANSANNULAR DIELS-ALDER REACTION;
D O I
10.1139/v90-329
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of the four acyclic trienes 11a, b and 20a, b is reported. The tandem macrocyclization and stereoselective transannular Diels-Alder reaction of acyclic trienes 11b (trans-trans-cis) and 20b (trans-trans-trans) were observed in the presence of Cs2CO3 at 85-degrees-C to give tricycles 30 (TST) and 32 (CAT) respectively. However, treatment of acyclic trienes 11a (cis-trans-cis) and 20a (cis-trans-trans) under the same conditions yielded the 14-membered macrocycles 21 and 23, which were stereoselectively transformed at 250-degrees-C into tricycles 22 (CST) and 24 (CAT) respectively in excellent yield.
引用
收藏
页码:2144 / 2152
页数:9
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  • [31] STEREOCONTROLLED CONSTRUCTION OF A.B.C.[6.6.6] TRICYCLE VIA TRANSANNULAR DIELS-ALDER REACTION OF 14-MEMBERED MACROCYCLE WITH ACETYLENE AS DIENOPHILE
    XU, YC
    CANTIN, M
    DESLONGCHAMPS, P
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (12): : 2137 - 2143