title: A concise total synthesis of (-)-maoecrystal Z.
abstract: The first total synthesis of (-)-maoecrystal Z is described. The key steps of the synthesis include a diastereoselective Ti(III)-mediated reductive epoxide coupling reaction and a diastereoselective Sm(II)-mediated reductive cascade cyclization reaction. These transformations enabled the preparation of (-)-maoecrystal Z in only 12 steps from (-)-γ-cyclogeraniol.
authors.affiliation: Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
authors.forename: Jacob Y
authors.initials: JY
authors.lastname: Cha
authors.forename: John T S
authors.initials: JT
authors.lastname: Yeoman
authors.forename: Sarah E
authors.initials: SE
authors.lastname: Reisman
mesh_terms: D045786:Diterpenes, Kaurane / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D045786:Diterpenes, Kaurane; C520391:maoecrystal Z