ORGN 691 |
| Tedanolide C is a newly reported member of the tedanolide family of marine macrolides, all members of which exhibit cytotoxicity in the picomolar to nanomolar range. Tedanolide C was isolated in 0.003% of the wet weight of the Papua New Guinea marine sponge Ircina sp. by Ireland and co-workers (2006). This new natural product resembles the previously isolated tedanolides in the fundamental structure of its 18-membered-ring macrolide core, yet differs in its substitution pattern and stereochemistry—particularly in the C1–C12 half of the molecule. The scarcity of tedanolides from their natural sources has limited the extensive biological evaluation of these potent anticancer compounds. We have developed a versatile approach to the C1–C12 fragment of tedanolide C which provides rapid access to the proposed stereochemistry as well as to several diastereomers. A key asymmetric hydroformylation step allows for late-stage stereodivergence.
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Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster
Sci-Mix
Division of Organic Chemistry |
