Formal total synthesis of selaginpulvilin D

Org Biomol Chem. 2017 Jul 19;15(28):5908-5911. doi: 10.1039/c7ob00950j.

Abstract

An efficient and mild synthetic strategy for the total synthesis of selaginpulvilin D has been reported. A highly chemoselective enyne-alkyne dehydro Diels-Alder reaction has been employed for the construction of the tricyclic fluorene framework present in the natural product selaginpulvilin D. An improved overall yield (10.5%) has been achieved for selaginpulvilin D, starting from commercially available m-anisaldehyde in 9 linear, operationally simple synthetic transformations.

MeSH terms

  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Cycloaddition Reaction
  • Molecular Structure
  • Polycyclic Compounds / chemical synthesis*
  • Polycyclic Compounds / chemistry
  • Stereoisomerism

Substances

  • Alkynes
  • Biological Products
  • Polycyclic Compounds
  • selaginpulvilin D