Approaches to the synthesis of 4-hydroxypiloquinone

R.G.F. Giles; P.R.K. Mitchell; M.V. Sargent

doi:10.1039/P19830002147

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Approaches to the synthesis of 4-hydroxypiloquinone

Journal article

Peer reviewed

Approaches to the synthesis of 4-hydroxypiloquinone

R.G.F. Giles, P.R.K. Mitchell and M.V. Sargent

Journal of the Chemical Society, Perkin Transactions 1, pp.2147-2152

1983

DOI: https://doi.org/10.1039/P19830002147

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Abstract

The synthesis of 4-acetoxy-1,8-dihydroxy-2-methyl-3-(4-methylpentanoyl)phenanthrene-9,10-quinoee (30) and 1,4,8-trimethoxy-2-methyl-3-(4-methylpentanoyl)phenanthrene-9,10-quinone (33), derivatives of the mould metabolite 4-hydroxypiloquinone [1,4,8-trihydroxy-2-methyl-3-(4-methylpentanoyl)-phenanthrene-9,10-quinone](2) are described. Photocyclization of methyl 2,2′,5,6′-tetramethoxy-3-methylstilbene-4-carboxylate (21) provided methyl 1,4,8-trimethoxy-2-methylphenanthrene-3-carboxylate (22), suitable for further elaboration into the natural derivatives.

Details

Title: Approaches to the synthesis of 4-hydroxypiloquinone
Authors/Creators: R.G.F. Giles (Author/Creator)
P.R.K. Mitchell (Author/Creator)
M.V. Sargent (Author/Creator)
Publication Details: Journal of the Chemical Society, Perkin Transactions 1, pp.2147-2152
Publisher: Royal Society of Chemistry
Identifiers: 991005543025407891
Murdoch Affiliation: Murdoch University
Language: English
Resource Type: Journal article

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