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Syntheses in enantiopure form of four diastereoisomeric naphthopyranquinones derived from aphid insect pigments

Aggarwal, R., Giles, R.G.F., Green, I.R., Oosthuizen, F.J. and Taylor, C.P. (2005) Syntheses in enantiopure form of four diastereoisomeric naphthopyranquinones derived from aphid insect pigments. Organic & Biomolecular Chemistry, 3 (2). p. 263.

Link to Published Version: http://dx.doi.org/10.1039/b414213f
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Abstract

The first syntheses are described of the four enantiopure naphthopyranquinones (1R,3R,4S)- and (1R,3R,4R)-3,4-dihydro-4,7,9-trihydroxy-1, 3-dimethylnaphtho[2,3-c]pyranquinone (quinone A 1 and quinone A' 2) and their two C-3 epimers, the (1R,3S,4S)- and (1R,3S,4R)-diastereoisomers 5 and 6, using enantiopure lactate as the source of asymmetry. Key factors in these syntheses are the maintenance of stereochemical integrity throughout the sequences and intramolecular diastereoselective cyclisations of the titanium phenolates of phenolic lactaldehydes. For these cyclisations the differing degree of diastereoselectivity is explained as are the stereochemistries of the product 2-benzopyran-4,5-diols.

Item Type: Journal Article
Murdoch Affiliation(s): School of Chemical and Mathematical Science
Publisher: Royal Society of Chemistry
URI: http://researchrepository.murdoch.edu.au/id/eprint/16065
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