A regio- and stereocontrolled total synthesis of (-)-allosamizoline is described. The key steps for this synthesis are ring-closing metathesis to form the cyclopentene core, halocyclization to afford the oxazoline ring, and finally stereoselective alkene radical addition followed by an alkene isomerization reaction to install the hydroxymethyl group. (-)-Allosamizoline was prepared in a total of 13 steps and 22% overall yield.
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Recent progress on synthesis and activities of allosamidin and its analogues.
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Org Lett
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Universität Potsdam, Institut für Chemie, P.O. Box 601553, 14415 Potsdam, Germany.
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