ORGN 243 |
| The aglycone structures 2 and 3. corresponding to the respective antitumor antibiotic natural products altromycin and kidamycin, have been efficiently synthesized from a common advanced intermediate 1. A series of Claisen condensations and aromatizations affords the anthracene section of 1, followed by annulation of the pyrone ring. From 1, the epoxide of 2 is generated by enantioselective dihydroxylation, O-deprotection and oxidation to anthraquinone, and substitution of a secondary mesylate to provide altromycin aglycone 2. Kidamycin aglycone 3 is obtained by nickel-catalyzed methyl addition to the derived aryl triflate of 1, followed by a similar sequence of O-deprotection and anthracene oxidation.
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Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- 202B, Oral
Division of Organic Chemistry |
