Perry Clark Heath

Synthesis of carbacephem antibiotics: synthesis via dieckmann reaction using phenyl esters to direct the regioselectivity of the cyclization

Abstract β-Ketoesters useful for elaboration to carbacephems were synthesized from a variety of enantiomerically pure diesters. Use of phenyl esters to direct the regioselectivity was demonstrated.

An efficient acylation/base-catalyzed cyclization of thioureas affords N,N′-disubstituted thiobarbituric acids

Abstract Acylation of 1,3-disubstituted thioureas with methyl malonyl chloride followed by base-catalyzed cyclization leads to the preparation of 1,3-disubstituted-2-thiobarbituric acids in high yield.

A diastereoselective tandem metalloenamine alkylation/aza-annulation of β-tetralones expedites the synthesis of benzoquinolinones

Abstract In one operation, metalloenamines derived from R -phenylethylamine (PEA) and a β-tetralone were treated with an electrophile followed by acrylic anhydride. The unpurified lactams were reduced to give 10b-angular benzoquinolinones (BQs).

Separation and purification of azetidinyl methyl sulfinates using preparative high-performance liquid chromatography

Abstract An improved method for the separation and purification of azetidinyl methyl sulfinates is described. This method utilizes a Waters preparative high-performance liquid chromatographic set-up. The methyl sulfinate isomers are isolated in high purity and no double bond isomerization is observed to occur. The diastereomers eluted from both the analytical and preparative columns at approximately the same retention times under the conditions used in the method.