A General Entry to Ganoderma Meroterpenoids: Synthesis of Applanatumol E, H, and I, Lingzhilactone B, Meroapplanin B, and Lingzhiol

Org Lett. 2024 Oct 25;26(42):9017-9021. doi: 10.1021/acs.orglett.4c03192. Epub 2024 Oct 11.

Abstract

Ganoderma meroterpenoids are fungal derived hybrid natural product class containing a 1,2,4-trisubstituted benzene ring and a polycyclic terpenoid part. The representatives applanatumol E, H and I, lingzhilactone B, and meroapplanin B share the same bicyclic lactone moiety connected to the arene. Employing photo-Fries rearrangements as the key step enabled a general entry to these natural products. For the synthesis of the tetracyclic framework of lingzhiol, we made use of a powerful photoredox oxidative decarboxylation/Friedel-Crafts sequence.

MeSH terms

  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Ganoderma* / chemistry
  • Lactones / chemical synthesis
  • Lactones / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Terpenes* / chemical synthesis
  • Terpenes* / chemistry

Substances

  • Terpenes
  • Biological Products
  • Lactones