Tetrahedron

DDQ induced oxidative cyclisations of 1, 2-dihydronaptho [2, 1-b] furans

M Jevric, DK Taylor, BW Greatrex, ERT Tiekink

Index: Jevric, Martyn; Taylor, Dennis K.; Greatrex, Ben W.; Tiekink, Edward R.T. Tetrahedron, 2005 , vol. 61, # 7 p. 1885 - 1891

Full Text: HTML

Citation Number: 8

Abstract

We have recently developed a route to 1,2-dihydronaptho[2,1-b]furans 3 utilising 1,2-dioxines 1 and stabilised phosphorus ylides. 10 We considered these products to be ideal substrates for DDQ induced oxidation due to the stabilising effect of the furan ring on the intermediate napthylic cation. The products generated in this previous study also contained an ester group that could act as the nucleophile for the intramolecular trapping of the napthylic cation. It was ...