A fully stereocontrolled total synthesis of (+)-leucascandrolide A |
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Authors: | Ian Paterson Matthew Tudge |
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Affiliation: | Department of Chemistry, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK |
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Abstract: | A highly stereocontrolled total synthesis of leucascandrolide A, a cytotoxic 18-membered macrolide from the calcareous sponge Leucascandra caveolata, starts out with a Jacobsen asymmetric hetero Diels-Alder reaction to configure the 2,6-cis-tetrahydropyran ring. All the remaining oxygenated stereocentres are introduced with high selectivity by relying on substrate-based control. An efficient endgame depends on two Mitsunobu reactions, the first to close the macrolactone with inversion at C17 and the second to attach the oxazole-containing side chain at C5, followed by Lindlar hydrogenation of the two alkynes to provide (+)-leucascandrolide A. |
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Keywords: | macrolides hetero Diels-Alder reaction aldol reaction Mitsunobu reaction cytotoxic antifungal |
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