Journal article
Syntheses of the aphid pigment derivatives quinone A, quinone A′, and deoxyquinone A as racemates
Journal of the Chemical Society, Perkin Transactions 1, (8), pp.2469-2476
1988
Abstract
3-Acetyl-5-methoxy-1,7-bisisopropoxy-4-naphthol (11) was converted in a number of high yielding transformations into the title quinones. Key steps were the stereospecific base-induced cyclisation in almost quantitative yield of 2-allyl-4,7-bisbenzyloxy-3-(1-hydroxyethyl)-1,5-dimethoxynaphthalene (18) into 7,10-bisbenzyloxy-3,4-dihydro-5,9-dimethoxy-trans-dimethyl-1H-naphtho[2,3-c]pyran (20) followed by the oxygenation of (20) to afford its two C-4 hydroxy epimers (23) and (26) in high combined yield, by potassium t-butoxide in dimethyl sulphoxide in the presence of oxygen. The efficient conversion of the major pseudoequatorial hydroxy compound (23) into the minor pseudoaxial hydroxy epimer (26)via the corresponding pseudoaxial chloro derivative was useful in providing increased quantities of precursors to quinone A′.
Details
- Title
- Syntheses of the aphid pigment derivatives quinone A, quinone A′, and deoxyquinone A as racemates
- Authors/Creators
- J.F. Elsworth (Author/Creator)R.G.F. Giles (Author/Creator)I.R. Green (Author/Creator)J.E. Ramdohr (Author/Creator)S.C. Yorke (Author/Creator)
- Publication Details
- Journal of the Chemical Society, Perkin Transactions 1, (8), pp.2469-2476
- Publisher
- Royal Society of Chemistry
- Identifiers
- 991005542698307891
- Copyright
- © 1988 Royal Society of Chemistry
- Murdoch Affiliation
- Murdoch University
- Language
- English
- Resource Type
- Journal article
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