A concise total synthesis of (+/-)-bakkenolide A by means of an intramolecular Diels-Alder reaction

Org Lett. 1999 Aug 26;1(4):663-5. doi: 10.1021/ol990747y.

Abstract

(+/-)-Bakkenolide A was prepared in five steps from ethyl 4-benzyloxyacetoacetate by sequential alkylations with tiglyl bromide nd cis-5-bromo-1,3-pentadiene, followed by an intramolecular Diels-Alder reaction as the key step. The known 7-epibakkenolide A and novel 10-epi- and 7,10-diepibakkenolide A stereoisomers were obtained as minor byproducts.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Asteraceae / chemistry
  • Insecticides / chemical synthesis*
  • Sesquiterpenes
  • Stereoisomerism

Substances

  • Antineoplastic Agents, Phytogenic
  • Insecticides
  • Sesquiterpenes
  • 4-Butyrolactone
  • bakkenolide A