title: Towards the Total Synthesis of Marineosin A: Construction of the Macrocyclic Pyrrole and an Advanced, Functionalized Spiroaminal Model.
abstract: Herein, we describe the enantioselective construction of the 12-membered macrocyclic pyrrole core4of marineosin A in 5.1% overall yield from (S)-propylene oxide. The route features a key Stetter reaction to install a 1,4-diketone, which is then subjected to Paal-Knorr pyrrole synthesis and ring closing metathesis (RCM) to afford macrocycle4.A divergence point in the synthetic scheme also enabled access to a highly functionalized spiroaminal model system8via an acid-mediated hydroxyketoamide cyclization strategy.
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, TN 37232-6600 (USA).
authors.forename: Leslie N
authors.initials: LN
authors.lastname: Aldrich
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, TN 37232-6600 (USA).
authors.forename: Cynthia B
authors.initials: CB
authors.lastname: Berry
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, TN 37232-6600 (USA).
authors.forename: Brittney S
authors.initials: BS
authors.lastname: Bates
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, TN 37232-6600 (USA).
authors.forename: Leah C
authors.initials: LC
authors.lastname: Konkol
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, TN 37232-6600 (USA).
authors.forename: Miranda
authors.initials: M
authors.lastname: So
authors.affiliation: Departments of Pharmacology & Chemistry, Vanderbilt Center for Neuroscience Drug Discovery, 12415D MRBIV, Vanderbilt University Medical Center.
authors.forename: Craig W
authors.initials: CW
authors.lastname: Lindsley
keywords: Stetter; alkaloid; marineosin A; metathesis; pyrrole