AUTOMATIC ASSEMBLY OF SKELETON STRUCTURES .3. STEREOSELECTIVE SYNTHESIS, STEREOCHEMISTRY, AND CYCLIZATION OF HA,ALPHA'-DIOXY-ALPHA,ALPHA'-DI-TERT-BUTYLGLUTARIC ACID

Stereoselective synthesis of ha,alpha'-dioxy-alpha,alpha'-di-tert-buty lglutaric acid hydroxyiminolactonitrile (3) was conducted by the react ion of dipivaloylmethane with HCN in ether. The corresponding hydroxyl acetonitrile (4) and amide (5), acid (6), and its ester (7), from whic h 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-cyanohyrin, th e cis-pseudo-a orientation of the functional substituents in 3-7 and 9 , and the structure of the dilactone 8 were confirmed by the H-1, C-13 NMR, IR and mass spectra.