title: Three-step synthesis of (±)-preussin from decanal.
abstract: A straightforward and stereoselective synthesis of the alkaloid preussin is described starting from decanal and diethyl 3-diazo-2-oxopropylphosphonate. The key steps are an aza-Michael reaction from an α,β-unsaturated diazoketone followed by a highly stereoselective Cu-catalyzed ylide formation and then a [1,2]-Stevens rearrangement. This strategy is feasible for extension to preussin analogues, demonstrating its utility for the rapid construction of all-cis-substituted pyrrolidines.
authors: Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970, São Carlos, SP Brazil.
authors: Isac G
authors: IG
authors: Rosset
authors: Rafael M P
authors: RM
authors: Dias
authors: Vagner D
authors: VD
authors: Pinho
authors: Antonio C B
authors: AC
authors: Burtoloso
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000841:Anisomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; C058280:preussin; C021170:decanaldehyde; D000841:Anisomycin