Brian John Wright

Wittig reactions on unprotected aldohexoses: Formation of optically active tetrahydrofurans and tetrahydropyrans

Abstract The addition of phosphonate-sulphone (1) to a series of pyranoses gives either five- or six-membered ring closed sulphones (e.g. (4) or (5)).

Synthesis of (±)-negamycin and of (±)-epinegamycin

Abstract The antibiotic negamycin and its diastereomer have both been synthesized in racemic form. The latter has been found to possess antibacterial activity, but at a lower level than negamycin itself.

Synthesis of potential inhibitors of the enzyme pantothenate synthetase

Three phosphinate salts (5), (6) and (7) were prepared as potential inhibitors of the enzyme pantothenate synthetase. The synthesis of compound (5) utilises a (diethoxymethyl)-protected phosphinate (8) as a new reagent for the formation of unsymmetrical phosphinic acids and esters. Initial P-alkylation of (8) followed by a selective deprotection sequence yields intermediate P-H phosphinates (16) and (21) which can be P-alkylated a second time. Enzyme assays have been performed with the target compound and the results are discussed.