Synthetic studies on cyathin terpenoids: enantioselective synthesis of the tricyclic core of cyathin through intramolecular Heck cyclisation

E Drège, C Tominiaux, G Morgant…

Index: Drege, Emmanuelle; Tominiaux, Cyrille; Morgant, Georges; Desmaele, Didier European Journal of Organic Chemistry, 2006 , # 21 p. 4825 - 4840

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Citation Number: 9

Abstract

Abstract An enantioselective synthesis of the tricyclic ketone (+)-5, which displays the carbon core of NGF-inducing cyathane diterpenes, has been completed according to a strategy in which the key step was the intramolecular Heck reaction of the AC subunit 49 establishing the crucial anti stereochemical relationship between the two angular substituents. The C-9 quaternary centre was set up by taking advantage of the enantioselective Michael addition ...