Organic & Biomolecular Chemistry 2011-07-07

Application of Nazarov type electrocyclization to access [6,5,6] and [6,5,5] core embedded new polycycles: an easy entry to tetrahydrofluorene scaffolds related to Taiwaniaquinoids and C-nor-D homosteroids.

Ritesh Singh, Gautam Panda

Index: Org. Biomol. Chem. 9 , 4782, (2011)

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Abstract

An easy, efficient and concise approach to tetrahydrofluorene [6,5,6]ABC tricyclic core embedded new polycycles has been achieved under relatively mild and catalytic Nazarov type electrocyclization conditions, using 2 mol% of Sc(OTf)(3) in anhydrous DCM (dichloromethane) at room temperature, with high yields. The generality of the reaction has been illustrated by synthesizing diverse polycycles embedded with rare heterotricyclic [6,5,5]ABC skeletons.