Stereocontrolled construction of ABC [6.6. 6] tricycle via transannular Diels-Alder reaction of 14-membered macrocycle with acetylene as dienophile

…, M Cantin, P Deslongchamps

Index: Xu, Yao-Chang; Cantin, Michel; Deslongchamps, Pierre Canadian Journal of Chemistry, 1990 , vol. 68, # 12 p. 2137 - 2143

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Citation Number: 9

Abstract

The syntheses of the acyclic dienynes 14 a (cis-trans-acetylene) and 14 b (trans-trans- acetylene) are described. The tandem macrocyclization and transannular Diels-Alder reaction of the allylic chloride 14 b was conducted in the presence of Cs2CO3 at 85° 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 14 a under the same conditions afforded 14- ...