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

R. Aggarwal; R.G.F. Giles; I.R. Green; F.J. Oosthuizen; C.P. Taylor

doi:10.1039/b414213f

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

Journal article

Peer reviewed

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

R. Aggarwal, R.G.F. Giles, I.R. Green, F.J. Oosthuizen and C.P. Taylor

Organic & Biomolecular Chemistry, Vol.3(2)

2005

DOI: https://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.

Details

Title: Syntheses in enantiopure form of four diastereoisomeric naphthopyranquinones derived from aphid insect pigments
Authors/Creators: R. Aggarwal (Author/Creator) - Murdoch University
R.G.F. Giles (Author/Creator) - Murdoch University
I.R. Green (Author/Creator) - University of the Western Cape
F.J. Oosthuizen (Author/Creator) - Murdoch University
C.P. Taylor (Author/Creator) - Murdoch University
Publication Details: Organic & Biomolecular Chemistry, Vol.3(2)
Publisher: Royal Society of Chemistry
Identifiers: 991005543238007891
Murdoch Affiliation: School of Chemical and Mathematical Science
Language: English
Resource Type: Journal article

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Collaboration types: Domestic collaboration; International collaboration
Citation topics: 1 Clinical & Life Sciences; 1.219 Cancer Drugs; 1.219.1527 Naphthoquinone Derivatives
Web Of Science research areas: Chemistry, Organic
ESI research areas: Chemistry