Abstract
Sensitized photooxidation of 5-cyano-1, 2-dihydropyridine derivative (3) afforded a crystalline and reactive endo-peroxide (4), and sulfur derivatives (5 and 6) as well as oxygen derivatives (9 and 10) were produced in good yield from this singlet oxygen adduct (4). 2-Methoxy derivative (9b) was found to be a good intermediate for production of 4-substituted compounds such as 5, 6, 7, 8, and 10, and 1-O-methyl-5-benzamido-5-deoxy-allopiperidinose (15a) and 1-O-methyl-5-benzamido-5-deoxyaltropiperidinose (17a) were synthesized from 13, which was obtained by the cis-dihydroxylation reaction of 9b. Formation of 9 from 4 was proved to be a multi-step reaction through 23 and 26.
