Gist-brocades N.v.

Akzo N.v.

Peter M Smid

Arthur F Marx

Pieter Gijsbert Weber

Willem J Van Zoest

Jan Verwey

Pieter Vellekoop

A process for the preparation of novel 14.alpha., 17.alpha.-dihydroxy-17.beta.-substituted steroids by reacting 14.alpha.-hydroxy-17-oxo-steroids with metal organic compounds and the use of the said novel steroids in the production of 14.alpha., 17.alpha.-methylenedioxy-pregnane derivatives.

14.alpha.,17.alpha.-dihydroxy-17.beta.-substituted steroids

A process is disclosed for the preparation of 17.beta.-hydroxy-3-oxo-l7.alpha.-pregn-4-ene-21-carboxylic acid .gamma.-lactone and 17.beta.-hydroxy-3-oxo-17.alpha.-pregna-4,6-diene-21-carboxylic acid .gamma.-lactone of the formula: ##STR1## wherein the dotted line between the 6-7 positions indicates an optional double bond, which is present in the latter compound, by reacting an androst-5-ene-17-one derivative with an organo-phosphorus compound. These lactones are valuable intermediates in the synthesis of spironolactone.

New process for the preparation

R-sulfoxides of the formulae ##STR1## wherein ##STR2## represents an usual penicillin or cephalosporin amide group and X is selected from the group consisting of hydrogen, hydroxy, an alkanoyloxy and the residue of a nucleophilic agent and their salts and esters are prepared by oxidation of the corresponding penicillins and cephalosporins to convert the sulfur atom in the ring to a sulfoxide group and separating and isolating the penicillin- or cephalosporin R-sulfoxide so formed from the reaction mixture or by acylation of the free amino group of the intermediate 6-aminopenicillanic acid R-sulfoxide and 7-aminocephalosporanic acid R-sulfoxide and derivatives. A preferred straight oxidation method is the photosensitized oxygenation method.

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Bleiswijk, Netherlands

Peter M Smid