title: Synthesis of the tricyclic core of labiatin A and australin A.
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.
authors: WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, University Avenue, Glasgow G12 8QQ, United Kingdom. stephen.clark@glasgow.ac.uk
authors: J Stephen
authors: JS
authors: Clark
authors: David
authors: D
authors: Vignard
authors: Andrew
authors: A
authors: Parkin
mesh_terms: D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D006575:Heterocyclic Compounds, 3-Ring; C568581:australin A; C568580:labiatin A