Journal article
Asymmetric diastereoselective syntheses of the aphid insect pigment derivatives quinone A and quinone A'
Tetrahedron Letters, Vol.42(33), pp.5753-5754
2001
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.
Details
- Title
- Asymmetric diastereoselective syntheses of the aphid insect pigment derivatives quinone A and quinone A'
- Authors/Creators
- R.G.F. Giles (Author/Creator)I.R. Green (Author/Creator)F.J. Oosthuizen (Author/Creator)C.P. Taylor (Author/Creator)
- Publication Details
- Tetrahedron Letters, Vol.42(33), pp.5753-5754
- Publisher
- Elsevier BV
- Identifiers
- 991005540407807891
- Copyright
- © 2001 Elsevier Science Ltd.
- Murdoch Affiliation
- School of Mathematical and Physical Sciences
- Language
- English
- Resource Type
- Journal article
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- Collaboration types
- Domestic collaboration
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- 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