ABSTRACT
A Lewis acid-catalyzed tandem reaction strategy for the construction of a dihydrophenalene-lactone tetracyclic skeleton has been disclosed. Starting with 2-naphthol-tethered ketones and active methylene esters, the tandem reaction catalyzed by Sc(OTf)3 proceeded well to afford an array of dihydrophenalene-fused lactones with moderate to high efficiency and diastereoselectivity. Moreover, the synthetic utility of this protocol was demonstrated by easy gram-scale preparation and diverse product transformations.
ABSTRACT
An efficient Brønsted acid-catalyzed tandem reaction has been developed for the construction of a dihydrophenalene skeleton bearing an all-carbon quaternary center. Starting with 2-naphthol-tethered ketones and indoles, the tandem reaction catalyzed by TsOH monohydrate proceeded smoothly with good to excellent efficiency through a double Friedel-Crafts alkylation process. Moreover, the synthetic utility of this method was demonstrated by easy gram-scale preparation and product transformations to fused hexacyclic compounds.