Stereocontrolled construction of ABC [6.6. 6] tricycle via transannular Diels-Alder reaction of 14-membered triene macrocycle

…, YC Xu, P Deslongchamps

Index: Cantin, Michel; Xu, Yao-Chang; Deslongchamps, Pierre Canadian Journal of Chemistry, 1990 , vol. 68, # 12 p. 2144 - 2152

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Citation Number: 4

Abstract

The synthesis of the four acyclic trienes 11 a, b and 20 a, b is reported. The tandem macrocyclization and stereoselective transannular Diels-Alder reaction of acyclic trienes 11 b (trans-trans-cis) and 20 b (trans-trans-trans) were observed in the presence of Cs2CO3 at 85° C to give tricycles 30 (TST) and 32 (CAT) respectively. However, treatment of acyclic trienes 11 a (cis-trans-cis) and 20 a (cis-trans-trans) under the same conditions yielded ...