154652-83-2Relevant academic research and scientific papers
Synthesis and characterization of phosphonic acid-substituted amino acids as excitatory amino acid receptor antagonists
Ornstein, Paul L.,Arnold, M. Brian,Allen, Nancy K.,Schoepp, Darryle D.
, p. 309 - 312 (2007/10/03)
Decahydroisoquitioline-3-carboxylic acids, substituted at C-6 with an acidic moiety such as a phosphonic, sulfonic or carboxylic acid or tetrazole, were prepared as antagonists of excitatory amino acid (EAA) receptors.
Stereoselective Synthesis of 6-Substituted Decahydroisoquinoline-3-carboxylates: Intermediates for the Preparation of Conformationally Constrained Acidic Amino Acids
Ornstein, Paul L.,Augenstein, Nancy K.,Arnold, M. Brian
, p. 7862 - 7869 (2007/10/02)
In this article we describe the stereoselective preparation of two 6-(hydroxymethyl) substituted decahydroisoquinoline-3-carboxylates, which are useful in the synthesis of a number of excitatory amino acid antagonists, e.g., (-)-1a (LY235959), (-)-2a (LY202157) and (-)-3a (LY293558).For example, the known ketone 4 was converted to either the (3SR,4aRS,6SR,8aRS)-alcohol 18 or the (3SR,4aRS,6RS,8aRS)-alcohol 21, the former via a stereoselective hydroboration reaction, the latter via a stereoselective enol ether hydrolysis followed by reduction.These C-6 epimeric alcohols were easily converted to a number of useful intermediates, e.g., aldehydes, bromides and iodides.If we used resolved keone 4, then these intermediates could be obtained in optically active form.In either racemic or non-racemic form, these intermediates provided access to a number of diastereomerically pure amino acids that were difficult to obtain by earlier routes.
