Synthesis of the monomeric unit of γ-actinorhodin

MA Brimble, LJ Duncalf, SJ Phythian

Index: Brimble, Margaret A.; Duncalf, Letecia J.; Phythian, Sara J. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 9 p. 1399 - 1403

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Citation Number: 31

Abstract

The first syntheses of the monomeric units of actinorhodin 19 and 5-epi-γ-actinorhodin 18 are described. The key steps involve addition of 2-trimethylsilyloxyfuran 14 to the 2- acetylnaphthoquinone 13 affording the adduct 15 which undergoes oxidative rearrangement to a pyranonaphthoquinone system 16 upon treatment with ceric ammonium nitrate. Naphthoquinone 13 is prepared from naphthol 11 which, in turn, is prepared via addition ...