Synthesis of the tricyclic core of labiatin A and australin A |
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Authors: | Clark J Stephen Vignard David Parkin Andrew |
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Institution: | WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ, United Kingdom. stephen.clark@glasgow.ac.uk |
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Abstract: | A concise synthesis of the tricyclic core of the marine diterpene natural products labiatin A and australin A has been accomplished. The key ring-forming transformation is a cascade reaction comprising generation of a copper carbenoid from a diazo ketone, intramolecular reaction of the carbenoid with a cyclic ether, and rearrangement of the resulting free oxonium ylide or its metal-bound equivalent with ring expansion of the original cyclic ether. |
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