Studies on the substituted 3-aminopropan-1-ol motif of lycoctonine class norditerpenid alkaloids: A novel route to 3-hydroxymethylcyclohex-2-enone

Article abstract of DOI:10.1016/S0040-4039(98)01857-7

Pursuing our interest in methyllcaconitine (MLA), we have designed a synthetic route to substituted ring-A of lycoctonine class norditerpenoid alkaloids. A novel synthesis of 3-hydroxymethylcyclohex-2-enone has been achieved starting from cyclohex-2-enone. Key reactions are: 1,2-addition of 1,3-dithiane followed by allylic rearrangement, 1,4-hydrocyanation, Wittig reaction and conversion into the substituted N-ethyl-3-aminopropan-1-ol motif of these neopentyl-like alcohols.