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

被引：12

作者：

XU, YC ^{[1
]}

CANTIN, M ^{[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/v90-328

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The syntheses of the acyclic dienynes 14a (cis-trans-acetylene) and 14b (trans-trans-acetylene) are described. The tandem macrocyclization and transannular Diels-Alder reaction of the allylic chloride 14b was conducted in the presence of Cs2CO3 at 85-degrees-C in one-pot to provide tricyclic product 16, with the two hydrogens in ring B being cis. On the other hand, treatment of the allylic chloride 14a under the same conditions afforded 14-membered macrocycle 17, which could be transformed at 250-degrees-C into a similar tricyclic product 18 with the two hydrogens in ring B being trans, along with an interesting by-product 19. The mechanism for the formation of 19 is also discussed.

引用

页码：2137 / 2143

页数：7

共 38 条

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