Total Synthesis of Bassiatin and Its Stereoisomers: Novel Divergent Behavior of Substrates in Mitsunobu Cyclizations
The Journal of Organic Chemistry2005Vol. 70(8), pp. 3079–3088
Citations Over TimeTop 25% of 2005 papers
Abstract
Total syntheses of the morpholine-2,5-dione, Bassiatin, and its stereoisomers have been completed. A key step in the syntheses was the Mitsunobu cyclization of hydroxyacid acyclic precursors. The hydroxyacid precursors are hindered alcohols and two substrates underwent Mitsunobu cyclization with retention of configuration. The other two substrates underwent Mitsunobu cyclization with either retention or inversion of configuration depending on reaction conditions. This divergence in outcome of the Mitsunobu reaction for the same substrate depending on effective concentration is novel.
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