title: Synthesis of the [5-7-6] tricyclic core of guanacastepene A via an intramolecular Mukaiyama aldol reaction.
abstract: [reaction: see text] A synthesis of the tricyclic [5-7-6] skeleton of guanacastepene A is described. The six-membered ring of guanacastepene A was constructed by a Diels-Alder reaction. After several functional group transformations, it was coupled to beta-iodocyclopentenone. Lithium dimethylcuprate conjugate addition followed by an intramolecular Mukaiyama aldol reaction furnished the desired [5-7-6] tricyclic ring system.
authors.affiliation: Department of Chemistry & Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, USA.
authors.forename: Xiaohui
authors.initials: X
authors.lastname: Du
authors.forename: Hiufung V
authors.initials: HV
authors.lastname: Chu
authors.forename: Ohyun
authors.initials: O
authors.lastname: Kwon
mesh_terms: D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D004224:Diterpenes; D007202:Indicators and Reagents; C409194:guanacastepene