title: Spiroaminal Model Systems of the Marineosins with Final Step Pyrrole Incorporation.
abstract: In this Letter, we describe a short, 6-step enantioselective route to spiroaminal lactam model systems reminiscent of marineosins A and B has been developed starting from either (R)- or (S)-hydroxysuccinic acid, respectively, in ~9% overall yield. This route enables late stage incorporation of the pyrrole ring at C5 via nucleophilic displacement of an iminium triflate salt.
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, TN 37232, USA ; Department of Pharmacology, Vanderbilt Center for Neuroscience Drug Discovery, Vanderbilt Specialized Chemistry Center (MLPCN), Vanderbilt University Medical Center, Nashville, TN 37232, USA.
authors.forename: Joseph D
authors.initials: JD
authors.lastname: Panarese
authors.forename: Leah C
authors.initials: LC
authors.lastname: Konkol
authors.forename: Cynthia B
authors.initials: CB
authors.lastname: Berry
authors.forename: Brittney S
authors.initials: BS
authors.lastname: Bates
authors.forename: Leslie N
authors.initials: LN
authors.lastname: Aldrich
authors.forename: Craig W
authors.initials: CW
authors.lastname: Lindsley
keywords: alkaloid; enantioselective; iminium triflate; marineosin; pyrrole