title: Synthesis of a ketone analogue of biotin via the intramolecular Pauson-Khand reaction.
abstract: We report an improved synthesis of 5-(5-oxohexahydrocyclopenta[c]thiophen-1-yl)pentanoic acid (ketone biotin, 1) based on the intramolecular Pauson-Khand cyclization. The synthesis proceeds in eight steps and in 2.7% overall yield from cyclohexene.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Room 18-496, Cambridge, Massachusetts 02139, USA.
authors.forename: Eric
authors.initials: E
authors.lastname: McNeill
authors.forename: Irwin
authors.initials: I
authors.lastname: Chen
authors.forename: Alice Y
authors.initials: AY
authors.lastname: Ting
mesh_terms: D001710:Biotin / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy
chemical_list: D007659:Ketones; D001710:Biotin