AUTOMATIC ASSEMBLY OF SKELETON STRUCTURES. 3. STEREOSELECTIVE SYNTHESIS, STEREOCHEMISTRY, AND CYCLIZATION OF d,l-α,α'-DIOXY-α,α'-DI-tert-BUTYLGLUTARIC ACID

Article abstract of DOI:10.1007/BF00864186

Stereoselective synthesis of d,l-α,α'-dioxy-α,α'-di-tert-butylglutaric acid hydroxyiminolactonitrile (3) was conducted by the reaction of dipivaloylmethane with HCN in ether.The corresponding hydroxylacetonitrile (4) and amide (5), acid (6), and its ester (7), from which dilactone (8) was synthesized with preparative yields, were obtained from 3.Benzyl amide (9) was obtained by the reaction of 8 with BnNH2.The iminolactone structure 3 of dipivaloylmethane bis-cyanohydrin, the cis-pseudo-a orientation of the functional substituents in 3-7 and 9, and the structureof the dilactone 8 were confirmed by the 1H, 13C NMR, IR and mass spectra.Keywords: stereoselective synthesis, stereochemistry, cyclization, γ-lactone, 1H and 13C NMR, mass spectra.