STUDIES ON THE SUBSTITUTED 3-AMINOPROPAN-1-OL MOTIF OF LYCOCTONINE CLASS NORDITERPENOID ALKALOIDS - A NOVEL ROUTE TO 3-HYDROXYMETHYLCYCLOHEX-2-ENONE

Pursuing our interest in methyllycaconitine (MLA), we have designed a synthetic route to substituted ring-A of lycoctonine class norditerpen oid alkaloids. A novel synthesis of 3-hydroxymethylcyclohex-2-enone ha s been achieved starting from cyclohex-2-enone. Key reactions are: 1,2 -addition of 1,3-dithiane followed by allylic rearrangement, 1,4-hydro cyanation, Wittig reaction and conversion into the substituted N-ethyl -3-aminopropan-1-ol motif of these neopentyl-like alcohols. (C) 1998 E lsevier Science Ltd. All rights reserved.