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Asymmetric diastereoselective syntheses of the aphid insect pigment derivatives quinone A and quinone A'

Giles, R.G.F., Green, I.R., Oosthuizen, F.J. and Taylor, C.P. (2001) Asymmetric diastereoselective syntheses of the aphid insect pigment derivatives quinone A and quinone A'. Tetrahedron Letters, 42 (33). pp. 5753-5754.

Link to Published Version: http://dx.doi.org/10.1016/S0040-4039(01)00955-8
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Abstract

Commercially available (R)-lactate has been used to provide the chiral source for the asymmetric diastereoselective syntheses of all four stereoisomers of 3,4-dihydro-4,7,9-trihydroxy-1,3-dimethylnaphtho[2,3-c]pyran-5,10-quinone based on 3R stereochemistry. The (1R,3R,4S) and (1R,3R,4R) stereoisomers were identical with the natural derivatives of the aphid insect pigments quinone A and quinone A′, while the (1S,3R,4S) and (1S,3R,4R) stereoisomers were found to be the enantiomers of two hitherto unreported naturally derived quinones from alternative aphid insect sources. A key-step is the titanium tetraisopropoxide-induced intramolecular diastereoselective cyclization of meta-hydroxybenzyl protected lactaldehydes to afford benzo[c]pyran-4,5-diols.

Item Type: Journal Article
Murdoch Affiliation(s): School of Mathematical and Physical Sciences
Publisher: Elsevier BV
Copyright: © 2001 Elsevier Science Ltd.
URI: http://researchrepository.murdoch.edu.au/id/eprint/35535
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