Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 32, Pages 9203-9208Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201504337
Keywords
antibiotic; natural products; structural revision; total synthesis; transannular Diels-Alder reaction
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Funding
- National Institutes of Health (USA) [AI055475]
- Cancer Prevention & Research Institute of Texas (CPRIT)
- Welch Foundation
- National Science Foundation Graduate Research Fellowship Program [DGE-1144086]
- Fulbright India
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The total synthesis and structural revision of antibiotic CJ-16,264 is described. Starting with citronellal, the quest for the target molecule featured a novel bis-transannular Diels-Alder reaction that casted stereoselectively the decalin system and included the synthesis of six isomers before demystification of its true structure.
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