ORGN 585 |
| Natural product Zincophorin is a valuable synthetic target both for its ionophore-type antibiotic activity as well as its imbedded anti, anti stereochemistry arduously achievable by other polypropionate methodologies. Our previous East-West approach based on elaboration of tetrahydropyran ring following polypropionate chain synthesis failed to introduce diastereoselectively the necessary 2,3-anti relationship (ratio of 3:1 at best). This project is aiming at an alternative West-East synthesis, where ring is first elaborated by an iodoetherification reaction followed by a stereocontrolled radical reduction in order to introduce the 7,8-syn relationship. Additionally, the other 7,8-anti diastereoisomer was obtained with excellent ratios (>20:1) showing the potential and versatility of such approach for the synthesis of complex tetrahydropyrans eventually extendable with a polypropionate chain to complete synthesis of Zincophorin and its analogues via an iterative tandem Mukaiyama aldolisation and radical reduction sequence.
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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
Division of Organic Chemistry |
