Synthesis of the monomeric unit of γ-actinorhodin
- 1 January 1997
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 9,p. 1399-1404
- https://doi.org/10.1039/a606765d
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 of furan 5 to 1,4-dimethoxy-2,3-dehydrobenzene followed by treatment with acid.Keywords
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