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

✍ Scribed by Xavier Doisy; Ian S. Blagbrough; Noel F. Thomas; Barry V.L. Potter

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 206 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)01857-7

✦ Synopsis

Pursuing our interest in methyllycaconitine (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.