A Convenient and Efficient Synthesis of (S)‐Lysine and (S)‐Arginine Homologues via Olefin Cross‐Metathesis.

Abstract

A convenient and efficient synthesis of (S)-lysine and (S)-arginine homologues via olefin cross-metathesis, Tetrahedron, 61(30), 2005, 7271-7276. Original journal article available here A convenient and efficient synthesis of (S)-lysine and (S)-arginine homologues via olefin cross-metathesis AbstractA convenient five step synthesis of (S)-homolysine, incorporating a key olefin cross-metathesis step in the chain extension methodology, has been developed, together with a six step related synthesis of a new homologue of arginine, (S)-bishomoarginine. Abstract: A convenient five step synthesis of (S)-homolysine, incorporating a key olefin crossmetathesis step in the chain extension methodology, has been developed, together with a six step related synthesis of a new homologue of arginine, (S)-bishomoarginine. A Convenient and Efficient Synthesis of (S)-Lysine and (S)-Arginine Homologues via Olefin Cross Metathesis

A Virtual Screening Hit Reveals New Possibilities for Developing Group III Metabotropic Glutamate Receptor Agonists

“…20 In the third strategy (method C, Scheme 3) the first P-C bond formation is similar to method B starting from aqueous hypophosphorous acid and protected vinylglycine or allylglycine to give the H-phosphinate derivatives 39 and 40 as previously described. 21 The second P-C bond formation is achieved by in situ generation of P III species by means of TMSCl or BSA 21 followed by a conjugate addition with a Michael acceptor (41,(44)(45)(46)(47)(48)(49)(50)(51)(52)56), a halide (42,43), or an aldehyde (53-55). Acidic hydrolysis and ion exchange chromatography purification afforded the desired amino acids [(S)-(þ)-1, 3, 4, 6, 7, 9-24; Scheme 3].…”