title: Practical and efficient approach to the synthesis of guineensine.
abstract: A total synthesis of guineensine, a secondary metabolite of the Piperaceae family, has been executed in 12 steps with an overall yield of 27%. Key steps in the synthesis featured novel application of a Julia-Kocienski olefination reaction which effectively constructed alkenamide skeleton. This contributes a unique approach to the synthesis of the piperamide alkaloids.
authors.affiliation: Organic Chemistry Division I, Natural Products Laboratory, Indian Institute of Chemical Technology, Hyderabad, India.
authors.forename: Shailesh D
authors.initials: SD
authors.lastname: Shingala
authors.forename: G Venkateswar
authors.initials: GV
authors.lastname: Reddy
authors.forename: R Sateesh Chandra
authors.initials: RS
authors.lastname: Kumar
authors.forename: P Ashok
authors.initials: PA
authors.lastname: Yadav
authors.forename: K Suresh
authors.initials: KS
authors.lastname: Babu
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D052117:Benzodioxoles / Q000737:chemistry; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D026321:Piperaceae / Q000737:chemistry
chemical_list: D000475:Alkenes; D000577:Amides; D052117:Benzodioxoles; D006574:Heterocyclic Compounds, 2-Ring; C492480:guineensine; C454279:retrofractamide A; C465333:retrofractamide-D