ORGN 71 |
| Racemic halofuginone (1), the active constituent of the veterinary drug Stenerol, is used as a feed additive to prevent protozoal infections in cattle and poultry. It was discovered through the derivitization of the antimalarial natural product (+)-febrifugine (2). Further biological studies of halofuginone have revealed the alkaloid possesses anti-angiogenic activity and racemic halofuginone is currently in Phase II clinical trials for bladder cancer. This first reported enantioselective synthesis of halofuginone features the 1,3-dipolar cycloaddition of allylic quinazinolone 3 and nitrone 4 to provide the key bicyclic hydroxylamine 5.
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Asymmetric Reactions and Syntheses
1:00 PM-5:00 PM, Sunday, 10 September 2006 Moscone Center -- Room 131, Oral
Division of Organic Chemistry |
