A Meisenheimer rearrangement approach to bridgehead hydroxylated tropane alkaloid derivatives

Article abstract of DOI:10.1016/0040-4039(95)02082-9

Thermolysis of 3-t-butyldimethylsiloxy-8-methyl-8-azabicyclo[3.2.1]oct-6-ene N-oxide (11) and (12) in butyronitrile gave 3-t-butyldimethylsiloxy-9-methyl-8-oxa-9-azabicyclo[3.2.2]non-6-ene (13) which upon reductive N-O ring cleavage, hydrogenation, oxidation and deprotection yielded the 3-hydroxy analogue 8-methyl-8-azabicyclo[3.2.1]octane-1,3-diol (6a ? 6b) of the tropane alkaloid physoperuvine.