Catalog Home Page

Syntheses of the aphid pigment derivatives quinone A, quinone A′, and deoxyquinone A as racemates

Elsworth, J.F., Giles, R.G.F., Green, I.R., Ramdohr, J.E. and Yorke, S.C. (1988) 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.

Link to Published Version: http://dx.doi.org/10.1039/P19880002469
*Subscription may be required

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′.

Publication Type: Journal Article
Publisher: Royal Society of Chemistry
Copyright: © 1988 Royal Society of Chemistry
URI: http://researchrepository.murdoch.edu.au/id/eprint/35693
Item Control Page Item Control Page