ORGN 419 |
| Linda C. Passaro and Steven K Pollack. Center for Bio/Molecular Science and Engineering, Code 6930, Naval Research Laboratory, 4555 Overlook Avenue, SW, Washington, DC 20375 |
| Current antifoulant technologies have been found to be both harmful to marine life and to the environment. As a result, there is now an urgent need for new antifoulant technology that both effectively prevents organism growth and is environmentally friendly. Naturally occurring antifoulant compounds, those expressed by marine organisms, are only available in limited amounts and often their structural complexity makes synthetic production in large quantities difficult. One analog of a naturally occurring antimicrobial agent, 2-furyl-n-pentyl ketone, has been a popular synthetic target. An alternative synthesis has been developed using lithiodithiane chemistry. Conversion of the carbonyl group into a 1,3-dithiane moiety offers a stable intermediate that can easily be lithiated and reacted with various electrophiles to afford the desired extended alkyl chain analogs. The resulting 1,3-dithiane derivative can easily be hydrolyzed using various conditions to give the preferred carbonyl compound. |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Division of Organic Chemistry |