Osamu Oda

An expeditious synthesis of pentosidine, an advanced glycation end product

Abstract The chemical synthesis of pentosidine (1), an advanced glycation end product, was achieved via the asymmetric alkylation of the chiral schiff base derived from (+)-2-hydroxy-3-pinanone ((+)-HyPN) and glycine tert-butyl ester, the mercury salt mediated intramolecular guanylation, and the regioselective alkylation of imidazo[4,5-b]pyridine ring. This reliable synthetic achievement will promise availability of pentosidine (1) in quantities.

Efficient total synthesis of pentosidine, an advanced glycation endproduct

Abstract The efficient total synthesis of pentosidine (1), an advanced glycation endproduct, was achieved using the asymmetric alkylation of a chiral schiff base (2), the intramolecular guanylation with mercury (II) chloride, and the quaternization accompanied by removal of the trityl group as key steps.

Sodium bis(2-methoxyethoxy)(1,1,1,3,3,3-hexafluoro-2-propoxy)aluminum hydride, a new stereoselective reducing agent in a carbacyclin synthesis

Abstract A new reducing agent ( 2j ) reduced the enone ( 4 ) to give 15( S )-allylic alcohol ( 5a ) with excellent regio- and stereoselectivity through a five membered ring transition state. Stereoselecrivity of this reaction will be explained based on the LUMO of the enone moiety. The resulting ( 5a ) was led to a carbacyclin.