Jeffrey S. Sabol

A new method for the electrophilic fluorination of vinyl stannanes

Abstract A new method for the electrophilic fluorination of vinyl stannanes using commercially available 1-chloromethyl-4-fluoro-1,4- diazoniabicyclo[2.2.2]octane bis-(tetrafluoroborate) (1) has been developed.

Constrained amino acids. An approach to the synthesis of 3-substituted prolines

Abstract The synthesis of diastereomeric substituted proline peptidomimetics as conformationally restricted tyrosine derivatives 1a,b has been accomplished utilizing the intramolecular hydroboration-cycloalkylation of azido-olefins 7a,b as the key step.

A new route to 1,1-difluoro olefins: Application to the synthesis of 2′-deoxy-2′-difluoromethylene nucleosides.

Abstract Methodology has been developed for the difluoromethylenation of ketone 2 , resulting in the synthesis of cytidine derivative 1c .

Conformationally restricted leukotriene antagonists. Asymmetric synthesis of some nor-leukotriene D4 analogs

Abstract The enantiomeric pair of conformationally-restricted nor-LTD 4 analogs 10 and 11 have been synthesized stereoselectively from (S)-2-cyclohexen-1-ol.

The synthesis of (1-fluorovinyl)tributyltin: A synthetic equivalent for the 1-fluoroethene anion

Abstract The synthesis of (1-fluorovinyl)tributyltin ( 1b ) is reported, and the utility of 1b as a synthetic equivalent for the 1-fluoroethene anion 2 through palladium-catalyzed couplings is demonstrated.

Improved Synthesis of (E)-2′-Deoxy-2′-(fluoromethylene)cytidine - A Potent Inhibitor Of Ribonucleotide Diphosphate Reductase

Abstract An improved synthesis of 1 is reported that utilizes cytidine as starting material and incorporates the stereospecific method to fluoro olefins as in the original process. The new route is five steps, compared to the seven step original procedure, with an overall yield of 29%. Several intermediates are crystalline and readily purified.

Syntheses of DL-2-fluoromethy-p-tyrosine and DL-2-difluoromethyl-p-tyrosine as potential inhibitors of tyrosine hydroxylase

Abstract The syntheses of the title compounds from 3,4-dimethylanisole and ethyl 5-hydroxy-2-methylbenzoate, respectively, are described.

Constrained amino acids. The synthesis of glutamine mimetics

Abstract The preparation and utility of conformationally constrained homoserines trans- 8 a and cis- 8b as intermediates for the synthesis of constrained glutamine mimetics trans- 1 a and cis- 1 b is presented.

Conformationally restricted leukotriene antagonists. Asymmetric synthesis of a nor-leokotriene D4 analog. II.

Chiral diol 5 is prepared from cyclohexanone and used in the asymmetric synthesis of nor-leukotriene D4 analog 1.

Fluorinated amino acids Part 3: Synthesis of β-difluoromethyl-m-tyrosine☆

Abstract The difluoromethyl carboxylic acid S -(+)- 9 was synthesized to assign the absolute configuration of diastereomers 2a and 2b , and the completion of the synthesis of β-difluoromethyl- m -tyrosines 1a,b is reported.