Daniel J. Plata

The stereospecific preparation of an hydroxyethylene isostere precursor via a novel piperidine-2,5-dione template

Abstract Hydroxyethylene isostere precursor 2 was synthesized by stereochemical manipulation of a novel keto- lactam “template”. The final product was prepared in very high enantiomeric purity, in 23% overall yield from L- phenylalanine.

A facile method for the preparation of MOM-protected carbamates.

A novel method for the preparation of MOM-protected carbamates is described that avoids the use of MOM-Cl, a regulated carcinogen. The two-step, one-pot procedure generates a reactive N-chloromethyl carbamate that is quenched with methanol to afford MOM-protected carbamates. The process is tolerant of a variety of functionalities, including Boc, sulfonamide, and acetamide protecting groups. Mild conditions for the removal of the MOM group are also described; selective deprotection of the MOM group in the presence of a Boc group has been demonstrated.

SYNTHESIS OF A-79175 : A SECOND GENERATION 5-LIPOXYGENASE INHIBITOR

Abstract A convergent, high yielding, and scalable synthesis of A-79175, with a key step involving a mild and efficient CuPd catalyzed coupling reaction of a terminal acetylene with a substituted 2-iodofuran is discussed.