Concise and very efficient synthesis of the N-methylwelwistatin tetracyclic core based on an anionic domino process

Org Biomol Chem. 2010 Oct 21;8(20):4521-3. doi: 10.1039/c0ob00382d. Epub 2010 Aug 18.

Abstract

An efficient synthesis of the N-methylwelwistatin tetracyclic core in only two steps from Kornfeld's ketone is described, whose key transformation involves the generation of a fused bicyclo[4.3.1]decane ring system through a one-pot sequence comprising a Michael-intramolecular aldolization anionic domino process and a DBU-promoted hydrolysis of the N-pivaloyl protecting group. Besides providing the most efficient synthesis of the welwistatin core to date, this method has the advantage of installing an oxygenated function at the welwistatin D ring.

MeSH terms

  • Alkaloids / chemical synthesis*
  • Anions
  • Bridged Bicyclo Compounds / chemistry
  • Catalysis
  • Hydrolysis
  • Indole Alkaloids
  • Temperature

Substances

  • Alkaloids
  • Anions
  • Bridged Bicyclo Compounds
  • Indole Alkaloids
  • welwitindolinone C isothiocyanate