Anthracyclines. XI. A short, site-specific synthesis of unsymmetrical 3-Acetyl-5, 8-dialkoxy-1, 2-dihydronaphthalenes; key precursors to daunomycinone AB-synthons

RA Russell, GJ Collin, MP Crane, PS Gee…

Index: Russell; Collin; Crane; et al. Australian Journal of Chemistry, 1984 , vol. 37, # 8 p. 1721 - 1728

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Citation Number: 5

Abstract

Abstract 5, 8-Dihydronaphthalene-1, 4-diol, readily available from benzoquinone and buta- 1, 3-diene, is isomerized by heating with strong sodium hydroxide, and acetylated (Ac 2 O), in situ, to form 5, 8-diacetoxy-1, 2-dihydronaphthalene. Catalysed (AlCl 3) addition of acetyl chloride followed by dehydrochlorination (LiCI/HCONMe 2) yielded 5, 8-diacetoxy-3-acetyl- 1, 2-dihydronaphthalene (11) in 82% overall yield. Base hydrolysis of (11), followed by ...