An aza-Achmatowicz approach toward the hydroxylated piperidine alkaloids (+/-)-azimic acid and (+/-)-deoxocassine.
[reaction: see text] The synthesis of several cis-2,3,6-trisubstituted piperidines has been developed employing the aza-Achmatowicz oxidation as the key reaction step. Its usage is illustrated by the facile synthesis of the piperidin-3-ol alkaloids (+/-)-deoxocassine and (+/-)-azimic acid.
Cassidy
Michael P
MP
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Padwa
Albert
A
D000470:Alkaloids / Q000138:chemical synthesis; D001372:Aza Compounds / Q000737:chemistry*; D006900:Hydroxylation; D008956:Models, Chemical; D010084:Oxidation-Reduction; D010880:Piperidines / Q000138:chemical synthesis*
D000470:Alkaloids; D001372:Aza Compounds; D010880:Piperidines; C502384:azimic acid; C492728:deoxocassine