Tetrahedron

Stereoselective synthesis of deoxy analogues of the 3C-protease inhibitor thysanone

MA Brimble, RJR Elliott

Index: Brimble, Margaret A; Elliott, Richard J.R Tetrahedron, 2002 , vol. 58, # 1 p. 183 - 189

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Citation Number: 28

Abstract

The synthesis of racemic 7, 9-dideoxythysanone 9 was achieved starting from allylnaphthalene 5 via epoxidation and reduction to bromoalcohol 7. Subsequent lithiation of the bromide and quenching with DMF afforded lactol 8 which underwent clean oxidative demethylation to racemic 6, 8-dideoxythysanone 9. The synthesis of (1R, 3S)-(+)-7, 9- dideoxythysanone 9 was then achieved albeit in low ee, starting from (R)-epoxide 6 which ...