Abstract
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.
Keywords:
antibiotic; natural products; structural revision; total synthesis; transannular Diels-Alder reaction.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Anti-Bacterial Agents / chemical synthesis*
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Biological Products / chemical synthesis
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Biological Products / chemistry
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Crystallography, X-Ray
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Cycloaddition Reaction
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Lactones / chemical synthesis*
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Lactones / chemistry
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Molecular Conformation
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Naphthalenes / chemistry
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Pyrazoles / chemical synthesis*
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Pyrazoles / chemistry
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Stereoisomerism
Substances
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Anti-Bacterial Agents
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Biological Products
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CJ-16,264
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Lactones
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Naphthalenes
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Pyrazoles
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decalin