title: Enantioselective Construction of the ABCDE Pentacyclic Core of the Strychnos Alkaloids.
abstract: An efficient enantioselective 12-step synthesis of the ABCDE pentacyclic core of the Strychnos alkaloids is described. A key feature of this approach is an organocatalyzed enantioselective desymmetrization to generate the morphan core in high ee and dr. After palladium-catalyzed installation of the indole moiety, a subsequent 5-exo-trig dearomatizing atom transfer radical cyclization was developed to construct the C-ring. Following a series of functional group interconversions, the pentacyclic amine core was obtained with all the relevant architecture including five stereocenters pertaining to the Strychnos alkaloids.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Mansfield Road, Oxford, OX1 3TA, U.K.
authors.forename: Adam D
authors.identifier: 0000-0002-3627-7525
authors.initials: AD
authors.lastname: Gammack Yamagata
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Mansfield Road, Oxford, OX1 3TA, U.K.
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon