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Convenient syntheses of the naturally occurring benzo[b]xanthen-12-one bikaverin. X-Ray crystallographic confirmation of the product regiochemistry

de Koning, C.B., Giles, R.G.F., Engelhardt, L.M. and Whitet, A.H. (1988) Convenient syntheses of the naturally occurring benzo[b]xanthen-12-one bikaverin. X-Ray crystallographic confirmation of the product regiochemistry. Journal of the Chemical Society, Perkin Transactions 1 (12). pp. 3209-3216.

Link to Published Version: http://dx.doi.org/10.1039/P19880003209
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Abstract

The synthesis of bikaverin (6,11-dihydroxy-3,8-dimethoxy-1-methylbenzo[b]xanthene-7,1 0,12-trione)(1) by two related routes is reported. Key steps include the formation of 1,2,4,5,8-pentamethoxynaphthalene (4) in good yield and its regiospecific acylation at C-6 with 2-benzyloxy-4-methoxy-6-methylbenzoic acid. Different methods are used to convert the derived orsellinylnaphthalene into 2,3-dihydro-5,8-dihydroxy-6,6′-dimethoxy-4′-methylnaphthalene-2-spiro2′-2′H-benzofuran-1,3′,4-trione (23) and the corresponding 5,6,6′,8-tetramethoxy analogue (25). Pyrolysis of these spiro compounds gives high yields of bikaverin from (23) and 6,11 -dihydroxy3,7,8,10-tetramethoxy-1-methylbenzo[b]xanthen-12-one (27) from (25). Compound (27) is readily converted into bikaverin.

Publication Type: Journal Article
Publisher: Royal Society of Chemistry
Copyright: © 1988 Royal Society of Chemistry
URI: http://researchrepository.murdoch.edu.au/id/eprint/35746
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