Synthesis in the field of podophyllotoxin and related analogues: Part XII-Synthesis of benzodioxan analogue of didemethoxy-beta-apopicropodophyllin

S Shashikanth, GL Hegde

Index: Shashikanth; Hegde, Ganesh L. Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004 , vol. 43, # 8 p. 1713 - 1720

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Abstract

The benzodioxan analogue of didemethoxy-beta-apopicropodophyllin 15 has been synthesized starting from 6. On Stobbe condensation of 2, 3-dihydro-benzo1, 4] dioxin-6-yl- (4-methoxyphenyl) methanone 6 with diethyl succinate gives 7 which on reduction with sodium amalgam yields 8. Cyclisation of 8 with PPA furnishes tetralone ester 10. Formylation of 10 with ethyl formate and sodium hydride affords 11, which on sodium ...