Saturday, 7 October 2006 - 11:10 AM
Kirkwood (Holiday Inn Binghamton - Arena)
542

An Asymmetric Approach to Oxetin via Serine Derived 2-Methyleneoxetanes

Marisa L. Blauvelt and Amy Ruth Howell. University of Connecticut, Storrs, CT

Oxetin, a ß-amino acid isolated from Streptomyces sp. OM-2317 in 1984, has demonstrated both herbicidal and antibacterial properties. Additionally, Oxetin was shown to be a potent glutamine synthetase inhibitor. Such inhibitors have been shown to hinder cell-growth and ultimately to demonstrate antitumor activity. Although Oxetin has been synthesized twice in the past, one synthesis was lengthy and non selective, while the other was racemic. We will present our asymmetric route to Oxetin utilizing a 3-amino- 2-methyleneoxetane ring, 1, derived from L-serine in just 3 steps.


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