Journal
TETRAHEDRON
Volume 67, Issue 27-28, Pages 5054-5068Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.04.002
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Funding
- Australian Research Council
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The formal total synthesis of the myxobacteria metabolite (-)-apicularen A (1) is described. The key step utilized to construct the 2,6-trans-disubstituted tetrahydropyran ring was the transannular oxy-Michael addition of enone (+)-48 to form trans-pyranone (+)-50. Cyclisation of the C13 epimer (-)-49 also gave the same trans-pyranone (+)-50 demonstrating that the stereochemistry of the apicualren ring system can be controlled only by the C15 asymmetric centre. Reduction of the ketone in (+)-50 and demethylation gave the advanced apicularen intermediate 4 completing the formal total synthesis of the natural product 1. (C) 2011 Elsevier Ltd. All rights reserved.
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