Yoshinori Tamura

Total Synthesis of Terprenin, a Highly Potent and Novel Immunoglobulin E Antibody Suppressant

Regioselective halogenations and Suzuki reactions ensure proper linkage of the aromatic rings in two total syntheses of terprenin (1). Both routes make it possible to prepare 1 efficiently and in large quantity.

Practical synthesis of L-erythro- and L-threo-4-fluoroglutamic acids using aminoacylase

Abstract Enantiomerically pure L- erythro - and L- threo -4-fluoroglutamic acids 1a and 1b were conveniently prepared. The key steps in this synthesis relied upon separation of diastereomers of N -chloroacetyl-4-fluoroglutamic acid 5-methyl ester 7 by recrystallization and enzymatic resolution of enantiomers of the resulting 7(a+c) and 7(b+d) by aminoacylase. Protection of the γ-carboxyl group as a methyl ester was found to be crucial for this enzymatic reaction.

Totalsynthese von Terprenin, einem hochwirksamen Immunglobulin-E-Suppressivum

Regioselektive Halogenierungen und Suzuki-Reaktionen ermoglichen die richtige Verknupfung der aromatischen Ringe in zwei Totalsynthesen von Terprenin 1. Durch beide Reaktionswege kann 1 effizient und in groserer Menge erhalten werden.