title: Total synthesis of diazonamide A.
abstract: A total synthesis of the marine natural product diazonamide A (1) has been accomplished. This work features a highly stereoselective synthesis of the C(10) quaternary center and the central furanoindoline core enabled by an iminium-catalyzed alkylation-cyclization cascade. Additionally, a magnesium-mediated intramolecular macroaldolization and a palladium-catalyzed tandem borylation/annulation were developed to enable the closure of the two 12-membered macrocycles of diazonamide A. This synthesis involves 20 steps in its longest linear sequence and proceeds in 1.8% overall yield.
authors.affiliation: Merck Center for Catalysis at Princeton University, Princeton, New Jersey, 08544, USA.
authors.forename: Robert R
authors.initials: RR
authors.lastname: Knowles
authors.forename: Joseph
authors.initials: J
authors.lastname: Carpenter
authors.forename: Simon B
authors.initials: SB
authors.lastname: Blakey
authors.forename: Akio
authors.initials: A
authors.lastname: Kayano
authors.forename: Ian K
authors.initials: IK
authors.lastname: Mangion
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Sinz
authors.forename: David W C
authors.initials: DW
authors.lastname: Macmillan