ORGN 752 |
| We have developed the first total synthesis of manzacidin D. This synthesis features a highly diastereoselective iodocyclization of an olefinic isothioureas, and a novel method for conversion of an appropriately substituted thiourea to the corresponding formamidine. Subsequent to our racemic synthesis, we investigated a formal asymmetric synthesis of manzacidin D. Using Maruoka's asymmetric phase transfer catalyst, we were able to form the first stereocenter in high ee. Proceeding with the same synthetic sequence to the iodocyclization step showed no loss of enantiomeric excess, thus constituting a formal enantioselective synthesis of manzacidin D. |
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Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |