Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 3, Issue 2, Pages 263-273Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b414213f
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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.
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