Journal article
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
1988
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.
Details
- Title
- Convenient syntheses of the naturally occurring benzo[b]xanthen-12-one bikaverin. X-Ray crystallographic confirmation of the product regiochemistry
- Authors/Creators
- C.B. de Koning (Author/Creator)R.G.F. Giles (Author/Creator)L.M. Engelhardt (Author/Creator)A.H. Whitet (Author/Creator)
- Publication Details
- Journal of the Chemical Society, Perkin Transactions 1, (12), pp.3209-3216
- Publisher
- Royal Society of Chemistry
- Identifiers
- 991005546368307891
- Copyright
- © 1988 Royal Society of Chemistry
- Murdoch Affiliation
- Murdoch University
- Language
- English
- Resource Type
- Journal article
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