title: A Scalable Total Synthesis of (-)-Nakadomarin A.
abstract: The convergent total synthesis of the manzamine alkaloid (-)-nakadomarin A (1) is described. The retrosynthetic analysis recognized spirocycle 3, assembled via an organocatalyst-promoted Michael addition/cyclization between bicyclic lactam 4 and furan aldehyde 5, both accessible from achiral starting materials and on a multigram scale. Lactam 4 is assembled through an SN2'/reduction/Staudinger/retro-aza-Claisen sequence on scale. After spirocyclization, the synthesis of nakadomarin is completed in only six steps.
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627, United States.
authors.forename: Robert K
authors.initials: RK
authors.lastname: Boeckman
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627, United States.
authors.forename: Hui
authors.initials: H
authors.lastname: Wang
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627, United States.
authors.forename: Kyle W
authors.initials: KW
authors.lastname: Rugg
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627, United States.
authors.forename: Nathan E
authors.initials: NE
authors.lastname: Genung
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627, United States.
authors.forename: Ke
authors.initials: K
authors.lastname: Chen
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627, United States.
authors.forename: Todd R
authors.initials: TR
authors.lastname: Ryder