Synthesis of unnatural pentahydroxylated pyrrolizidines: 5-epi- and 5,7a-di-epi-hyacinthacine C1 |
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Authors: | Juan A Tamayo Francisco Franco Fernando Sánchez-Cantalejo |
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Institution: | Department of Medicinal and Organic Chemistry, Faculty of Pharmacy, University of Granada, 18071 Granada, Spain |
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Abstract: | Stereocontrolled synthesis of 5-epi- and 5,7a-di-epi-hyacinthacine C1 (7 and 8), two potential glycosidase inhibitors are described using α,β-unsaturated ketone 9 as homochiral starting material. The key step in the synthesis is the highly diastereoselective dihydroxylation reaction of 9, that allows the obtention of a single bis-hydroxylated ketone (10). Further derivatization into two epimeric mesylate esters followed by internal cyclization form the pyrrolizidinic compounds 7 and 8. This type of compounds can be useful in glycobiology due to their ability to inhibit carbohydrate-processing enzymes. |
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Keywords: | Azasugars Hyacinthacines Enantioselectivity Synthetic methods Enzyme inhibitors |
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