title: Concise and stereocontrolled synthesis of the tetracyclic core of daphniglaucin C.
abstract: The tetracyclic core of daphniglaucin C was prepared from the known 4-keto-N-Boc methyl-l-prolinate in 15 steps with a cumulative yield of 14.7%. The key steps toward this core motif feature a reductive double bond transposition from an unactivated tertiary allylic alcohol, a Pd-catalyzed Stille coupling, and Dieckmann cyclizations.
authors.affiliation: Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Centre-ville, Montreal, QC, H3C 3J7, Canada. stephen.hanessian@umontreal.ca
authors.forename: Stephen
authors.initials: S
authors.lastname: Hanessian
authors.forename: Stéphane
authors.initials: S
authors.lastname: Dorich
authors.forename: Helge
authors.initials: H
authors.lastname: Menz
mesh_terms: D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D010165:Palladium / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001952:Bridged-Ring Compounds; D011083:Polycyclic Compounds; C585707:daphniglaucin C; D010165:Palladium