Marine Puupehenone and Puupehedione: Synthesis and Future Perspectives

Mar Drugs. 2023 May 26;21(6):322. doi: 10.3390/md21060322.

Abstract

Puupehenone and puupehedione are natural products isolated from marine organisms. These compounds display a broad spectrum of biological activities, the in vitro antitubercular activity of puupehenone being a stand out, and are equipped with an interesting structural complexity. These products have served to stimulate the continual interest of the synthetic community. The first part of this article is a review of their total synthesis, using natural compounds which have the potential to be transformed into these marine compounds as starting materials; the synthetic routes employed to generate the basic skeleton; and the advances made to synthesize the pyran C ring with the required diastereoselectivity to obtain the natural products. Finally, this perspective shows a personal reflection of the authors on a possible unified and efficient retrosynthetic route that could allow easy access to these natural products, as well as their epimers at the C8 carbon and which could be used to address future biological issues in the production of pharmacologically active compounds.

Keywords: marine natural products; meroterpenoids; puupehedione; puupehenone.

Publication types

  • Review

MeSH terms

  • Antitubercular Agents
  • Biological Products* / chemistry
  • Biological Products* / pharmacology
  • Sesquiterpenes* / chemistry
  • Xanthones*

Substances

  • puupehenone
  • Biological Products
  • Antitubercular Agents
  • Sesquiterpenes
  • Xanthones