Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 52, Pages 14522-14526Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408055
Keywords
C-H oxidation; cycloaddition; gracilioether F; ketenes; total synthesis
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Funding
- Indiana University
- U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-AC02-06CH11357]
- National Science Foundation/Department of Energy [NSF/CHE-1346572]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1346572] Funding Source: National Science Foundation
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The first synthesis of gracilioether F, a polyketide natural product with an unusual tricyclic core and five contiguous stereocenters, is described. Key steps of the synthesis include a Lewis acid promoted ketene-alkene [2+2] cycloaddition and a late-stage carboxylic acid directed C(sp(3))-H oxidation. The synthesis requires only eight steps from norbornadiene.
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