抄録
Oxidation of 2-benzoyl-6-acetoxymethyl-3, 6-dihydro-1, 2-oxazine (7) with osmium tetroxide afforded a mixture of 4, 5-cis-glycols which were separated and characterized as benzoyl derivatives (8a and 9a). Similarly 7 was oxidized with potassium permanganate, yielding a 4α, 5α-dihydroxyl derivative (8b) as the major product along with its 4β, 5β-isomer (9b). On the other hand, treatment of 7 with pertrifluoroacetic acid gave a crystalline 4β, 5β-epoxide (12) and a syrupy 4α, 5α-epoxide (13) in a good yield. Further, 12 was treated with sodium azide in dimethylformamide to give a 5β-hydroxy-4α-azide (14a) and a 4β-hydroxy-5α-azide (15a). Conformational analysis of these synthesized compounds was carried out by nuclear magnetic resonance spectrometry. Attempted conversion of 8b or 14a into a 4, 5-epimine was not successful.
