A formal enantioselective synthesis of (+)-dodoneine via cyclic sulfate methodology
Srinivasu V.N. Vuppalapati, Siddamal R. Putapatri, and Srinivas Kantevari*
Organic Chemistry Division-II, Indian Institute of Chemical Technology, Hyderabad-500007, INDIA
E-mail: kantevari@yahoo.com, kantevari@gmail.com
Abstract
An enantioselective formal synthesis of (+)-dodoneine is described using the Sharpless asymmetric dihydroxylation and regioselective nucleophilic opening of cyclic sulfate as the key steps.
Keywords: Sharpless asymmetric dihydroxylation, dodoneine, cyclic sulfate methodology, enantioselective synthesis
Introduction
Dodoneine 1, [(R)-6-[(S)-2-hydroxy-4-(4-hydroxyphenyl)butyl]-5,6-dihydropyran-2-one], is a recently isolated •,•-unsaturated •-lactone from the methanolic extract of a plant hemi parasite, Tapinanthus dodoneifolius DC Danser (also known as African mistletoe) found on a sheanut tree in Loumbila, West Africa.1 The structure of 1 was determined from spectroscopic and X-ray crystallographic analysis of the camphorsulphonate derivative of dodoneine.
The compound (+)-Dodoneine 1 exhibited relaxing effect on preconstricted rat arotic rings. The unique as well as challenging structural feature of this class of compounds along with their potential biological activity has aroused great interest among synthetic organic and medicinal chemists.2
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