381670-63-9Relevant academic research and scientific papers
Chemoenzymatic synthesis of a tachykinin NK-2 antagonist
Allan, Graham,Carnell, Andrew J.,Hernandez, Maria Luisa Escudero,Pettman, Alan
, p. 8193 - 8202 (2007/10/03)
A non-peptide tachykinin antagonist has been synthesized in a short and efficient four step sequence starting from a chiral enol acetate, which was obtained in enantiomerically pure form by resolution using a lipase catalysed transesterification reaction. The biotransformation was optimized in terms of solvent, temperature and immobilization method used. Oxidative cleavage of the (+)-enol acetate to give the key aldehyde ester intermediate could be achieved indirectly by oxidative rearrangement to an enone followed by Baeyer-Villiger oxidation and ring opening, or by epoxidation, rearrangement and oxidative cleavage or most directly by ozonolysis. X-Ray crystallographic analysis of a camphanic ester derivative of an ester alcohol confirmed that the absolute configuration of the enol acetate was (S).
