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Syntheses of nitrile and methyl ester corresponding to racemic sarkomycin and of related compounds

Syntheses of nitrile and methyl ester corresponding to racemic sarkomycin and of related compounds

Tetrahedron 43(2): 317-322

Nitrile 6a and ester 12 corresponding to (dl)-sarkomycin, 6- and 7-membered rings analogue nitriles 6b, 6c, and 3-methyl substituted nitrile 6d were prepared. Conjugate addition of cyanotrimethyl silane to cyclic .alpha.-enones gave 3-trimethylsiloxy 2-cycloalkene carbonitriles. Their alkylation with chloromethyl phenyl sulfide followed by oxone oxidation to sulfones and sulfinic acid elimination on basic alumina led to .alpha.-methylene carbonyl compounds. Obtention of the ester 12 involved acetalization of 3-oxo 2-phenylthiomethyl cyclopentane carbonitrile, basic hydrolysis into acid, deacetalization, esterification, oxidation and elimination of sulfinic acid.

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