Synthesis of a ketone analogue of biotin via the intramolecular Pauson-Khand reaction.
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.
McNeill
Eric
E
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Room 18-496, Cambridge, Massachusetts 02139, USA.
Chen
Irwin
I
Ting
Alice Y
AY
D001710:Biotin / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy
D007659:Ketones; D001710:Biotin