950902-01-9Relevant academic research and scientific papers
Practical enzymatic desymmetrization of 2-(ethoxycarbonyl)propane-1,3-diyl dihexanoate and model cyclization for the A-D ring system of lysergic acid
Miyata, Sachiho,Kumamoto, Takuya,Ishikawa, Tsutomu
, p. 1420 - 1438 (2008/02/08)
Porcine pancreas lipase-catalyzed hydrolysis of symmetrical 2-(ethoxycarbonyl)propane-1,3-diyl dihexanoate, under the modified conditions of the Seebach protocol, afforded a desymmetrized monohexanoate in 40-51% yield with 91-94% ee, even in a gram-scale reaction. The absolute configuration of a half-hydrolyzed (-)-product was determined to be (R) by conversion to a known 2-methylpropane-1,3-diol derivative. Samarium iodide-induced radical cyclization of 2-oxo-3-phenylethylamine with a C4 unit on the N-atom, derived from the racemic monohexanoate, afforded a 3-phenylpiperidine derivative as a model construction of the A-D ring system of lysergic acid.
