Location of Repository

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

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

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′

Publisher: Royal Society of Chemistry
Year: 1988
OAI identifier: oai:researchrepository.murdoch.edu.au:35693
Provided by: Research Repository
Download PDF:
Sorry, we are unable to provide the full text but you may find it at the following location(s):
  • http://researchrepository.murd... (external link)
  • http://researchrepository.murd... (external link)
  • http://researchrepository.murd... (external link)
  • http://researchrepository.murd... (external link)
  • Suggested articles


    To submit an update or takedown request for this paper, please submit an Update/Correction/Removal Request.