Bradford P. Mundy

A Facile Removal of the Tetrahydropyranyl Protecting Group from Alcohol Derivatives

Abstract The tetrahydropyranyl (THP) moiety has been frequently used as a protecting group for alcohols1. There has been an occasional comment regarding difficulty in storing the derivatives, since any trace of acid will hydrolyze them2. Also, as with any protecting group, one must be concerned with methods for its later removal3. In this report we describe a simple method for removing the THP protecting group under mild conditions and a procedure to store these derivatives.

Assignment of anomeric configuration and identification of carbohydrate residues by 13C nmr. 1. Galacto- and glucopyranosides and furanosidesl

Abstract A 13C NMR fingerprint method previously developed for galactosides and glucosides is extended to arabinosides and ribosides. This approach demonstrates the capability of 13C NMR to determine ring size and anomeric configuration in four isomeric arabinosides and ribosides.

Improved Synthesis of Various Isotope Labeled 4-Hydroxyalkenals and Peroxidation Intermediates

Abstract A concise and isotope specific synthesis of perfluorobenzyl 5,5,6,6-tetradeutero-9-oxononanoate and an abbreviated general multiisotope synthesis of 4-hydroxyalkenals is reported.

Novel of the sex pheromone of the Douglas-Fir Tussock Moth (orgyia pseudotsugata) and selonopsin a, a constituent of fire ant venom.

Abstract Use of a novel bicyclic ketal fragmentation protocol provides a simple entry into the sex pheromone of the tussock moth, as well as into the fire ant venom constituent, Solenopsin A.

A novel bicyclic ketal fragmentation reaction

Abstract Bicyclic ketals of the 6,8-dioxabicyclo[3.2.1]octane series are specifically cleaved to give δ, e-unsaturated ketones by treatment of the ketal with acetyl iodide.

A formal synthesis of modhephene

Abstract A stereo- and regiospecific synthesis of a propellane intermediate that has been previously converted to modhephene is reported.

A Cyclopentane, Cyclopentene and Cyclopentanone Annulation Methodology

Abstract The chemistry derived from the dienolates of 1,2-dicarboxylic acid esters is described. New methods for preparing cyclopentane, cyclopentene and cyclopentanone rings affixed to the diesters are discussed.

Synthesis of Deuterated 4-Hydroxyalkenals

Abstract A concise and isotope specific synthesis of deuterated analogs of 4-hydroxyalkenals is reported.

A New Approach to Pyrrolidine and Piperidine Alkaloids

Abstract An uhexpected success involving the rearrangement of N-benzoyl2-pyrrolidone(1)to 2-phenylpyrroline (2)1 provided us with an imaginative heuristic upon which some novel entries into the pyrrolidine and piperdine alkaloids was based.

Studies Directed Towards a Practical Synthesis of Brevicomins (II)1 : A Novel Synthesis of 1, 5-Dimethyl-8-Oxobicyclo [3.2.1]octane-6-one

Abstract The recent interest in pheromones,2 as means of controlling insect pests, has prompted us to examine syntheses which could be both simple and practical. We recently reported a three-step synthesis of brevicomin (3), the aggregating pheromone of the pine bark beetle, Dendroctonus brevicomis.3