title: Pauson-Khand adducts of N-Boc-propargylamine: a new approach to 4,5-disubstituted cyclopentenones.
abstract: A new approach to the synthesis of 4,5-disubstituted cyclopentenones is described. The strategy is based on the Pauson-Khand (PK) reaction of norbornadiene and N-Boc-propargylamine as an alkyne with a masked leaving group, which can be eliminated at will. This approach to the synthesis of 4,5-disubstituted cyclopentenones overcomes the problem of using the alkylation to introduce the α side chain. As an example, prostane 13-epi-12-oxo-phytodienoic acid (13-epi-12-oxo-PDA) methyl ester was synthesized.
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona), c/Baldiri Reixac, 10, 08028 Barcelona, Spain.
authors.forename: Nuria
authors.initials: N
authors.lastname: Aiguabella
authors.forename: Albert
authors.initials: A
authors.lastname: Pesquer
authors.forename: Xavier
authors.initials: X
authors.lastname: Verdaguer
authors.forename: Antoni
authors.initials: A
authors.lastname: Riera
mesh_terms: D000478:Alkylation; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry; D011437:Propylamines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D005231:Fatty Acids, Unsaturated; D011437:Propylamines; C009054:propargylamine; C025999:12-oxophytodienoic acid; D010293:Pargyline; C013905:cyclopentenone