1248586-85-7Relevant academic research and scientific papers
Synthesis of unnatural pentahydroxylated pyrrolizidines: 5-epi- and 5,7a-di-epi-hyacinthacine C1
Tamayo, Juan A.,Franco, Francisco,Sánchez-Cantalejo, Fernando
experimental part, p. 7262 - 7267 (2010/10/02)
Stereocontrolled synthesis of 5-epi- and 5,7a-di-epi-hyacinthacine C 1 (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.
