John E. Franz

Plant Growth Regulators

Large-scale use of plant growth-regulating chemicals, unheard of ten years ago, has fostered a multimillion dollar business. In 1948, 27 1/2 million pounds of 2,4-D, once used only in minute doses for laboratory work, were manufactured for agricultural use, primarily in weed eradication. Naphthaleneacetic acid and other compounds are used in smaller but continually increasing quantities in regulating other phases of plant development, wholly apart from nutritional needs supplied by fertilizers.

Design and synthesis of γ-oxygenated phosphinothricins as inhibitors of glutamine synthetase

The ability of L-γ-hydroxyglutamic acids to act as substrates of the enzyme glutamine synthetase (GS) was exploited as a rationale for the synthesis of γ-oxygenated analogues of the naturally occurring GS inhibitor phosphinothricin (PPT). The potent new inhibitor DL-γ-hydroxyphosphinothricin (GHPPT) was prepared via a key reaction involving the silicon-mediated addition of ethyl methylphosphinate to benzyl 2-benzyloxycarbonylamino-4-oxobutyrate. The resulting intermediate was also converted to various derivatives useful in probing structure–activity relationships in the GHPPT series. The γ-oxygenated phosphinothricins display enzyme inhibitory activity as well asin vivo phytotoxicity.

Preparation of Trifluoromethylsulfonylpyrroles via Mesoionic Intermediates

Abstract The reaction of N-substituted-N-formylglycine and phenyltrifluoromethylsulfonylacetylene in acetic anhydride results in the formation of substituted-4-trifluoromethylsulfonylpyrroles. In our continuing efforts1 to prepare novel hetero structures via mesoionic intermediates, we would like to report the general preparation of

A New Furan Synthesis. Evidence for the Intermediacy of the Elusive Anhydro-5-hydroxy-1,3-dioxolium Hydroxide System

Abstract While five-membered mesoionic ring systems have been employed as useful synthetic intermediates in the preparation of a wide variety of pyrroles and thiophenes1, only limited application has been made to the preparation of furans2. We would like to report a new furan synthesis in which the unreported anhydro-5-hydroxy-1, 3-dioxolium hydroxide system may be an intermediate.

Facile synthesis of 4-N-phosphonomethyl-2,4-diamino-butyrates as inhibitors of glutamine synthetase

Abstract An effective synthesis of N-substituted 2,4-diaminobutyric acids is described involving reaction of amines with methyl 4-bromo-2-phthalimidobutyrate, followed by hydrolysis. This approach was applied to the synthesis of 4- N -phosphonomethyl-2,4-diaminobutyric acids as inhibitors of glutamine synthetase.

Synthesis of Carbonyl Cyanide Alkylhydrazones

Abstract Carbonyl cyanide phenylhydrazone (CCP) is well known as an uncoupler of oxidative phosphorylation in mitochondrial systems.1 A large number of phenyl-substituted CCP derivatives have been prepared by the general route involving diazotization of the aniline and coupling the resulting diazonium ion with malononitrile.2

The Reaction of 1, 2-Disubstituted-3-Benzylglycerols and Trimethylsilyl Iodide (TMSI). Improved Method for the Preparation of 1, 2-Dialkylglycerols

Abstract A new efficient preparation of 1, 2-dialkylglycerols is reported. The method involves the reaction of the appropriate benzyl ether with trimethylsilyl iodide (TMSI).