title: Expedient Synthesis of (+)-Lycopalhine A.
abstract: Two amino acids play a key role in the first total synthesis of lycopalhine A. L-glutamic acid serves as a convenient chiral starting material for the 13-step synthesis, and l-proline promotes an unusual 5-endo-trig Mannich cyclization that generates the central pyrrolidine ring of the Lycopodium alkaloid. The bicyclo[3.3.0]octanol moiety of the molecule is formed through an intramolecular aldol addition that may occur spontaneously in nature.
authors.affiliation: Department of Chemistry, Ludwig-Maximilians-Universität München, 81377, Munich, Germany.
authors.forename: Benjamin M
authors.initials: BM
authors.lastname: Williams
authors.affiliation: Department of Chemistry, Ludwig-Maximilians-Universität München, 81377, Munich, Germany. dirk.trauner@lmu.de.
authors.forename: Dirk
authors.identifier: http://orcid.org/0000-0002-6782-6056
authors.initials: D
authors.lastname: Trauner
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; C000609720:lycopalhine A
keywords: Lycopodium alkaloids; Mannich reaction; aldol reaction; amino acids; total synthesis