title: Synthesis of putative uniflorine A.
abstract: A diastereoselective synthesis of the putative structure of the natural product uniflorine A has been achieved by using the Petasis borono-Mannich reaction and ring-closing metathesis as key steps. The NMR data of the synthetic material did not match that reported for the natural product. The structure of the final synthetic product was unequivocally determined by single-crystal X-ray study of its pentaacetate derivative. Thus it was concluded that the proposed structure of uniflorine A is incorrect.
authors.affiliation: Department of Chemistry, University of Wollongong, Wollongong, New South Wales, 2522, Australia.
authors.forename: Andrew S
authors.initials: AS
authors.lastname: Davis
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Pyne
authors.forename: Brian W
authors.initials: BW
authors.lastname: Skelton
authors.forename: Allan H
authors.initials: AH
authors.lastname: White
mesh_terms: D000085:Acetates / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis*; D000478:Alkylation; D018360:Crystallography, X-Ray; D003500:Cyclization; D007212:Indolizines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000470:Alkaloids; D007212:Indolizines; C487671:uniflorine A