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Terpenoid Synthesis via Convergent Radical Annulation.

Alex L Rerick1, Griffin L Barnes1, Fabian Schneider1

  • 1Department of Chemistry, Scripps Research, La Jolla, California, 92037, USA.

Angewandte Chemie (International Ed. in English)
|November 25, 2025
PubMed
Summary
This summary is machine-generated.

A new radical annulation strategy enables efficient synthesis of complex terpenoids. This method uses a 1,3-diradical synthon for rapid C-ring formation, simplifying the creation of intricate molecular scaffolds.

Keywords:
ElectrochemistryNatural productsOrganic synthesis

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Natural Product Synthesis

Background:

  • Terpenoids are complex natural products with diverse biological activities.
  • Efficient synthetic routes to complex terpenoid scaffolds remain a challenge in organic chemistry.

Purpose of the Study:

  • To develop a convergent radical annulation strategy for synthesizing complex terpenoids.
  • To showcase the utility of this strategy through the synthesis of serratene and cyclodammarane scaffolds.

Main Methods:

  • Utilized a 1,3-diradical synthon for C-ring annulation via radical couplings.
  • Employed rapid alternating polarity (rAP) Kolbe electrolysis for onoceradiene assembly.
  • Developed a Co-electrocatalytic metal-catalyzed hydrogen atom transfer (MHAT) for 7-endo-trig cycloisomerization.
  • Applied a tandem Fe-mediated reductive olefin coupling/enolate alkylation cascade for propellane motif construction.

Main Results:

  • Achieved concise syntheses of serratene and cyclodammarane scaffolds from a common intermediate.
  • Demonstrated the first Co-electrocatalytic MHAT 7-endo-trig cycloisomerization to form the serratene core.
  • Reported an unprecedented tandem cascade for constructing the cyclodammarane propellane motif with high diastereocontrol.
  • Completed syntheses in 5-9 steps, maximizing skeletal bond-forming efficiency.

Conclusions:

  • The developed radical annulation strategy offers an efficient and versatile approach to complex terpenoids.
  • Highlighted the power of radical-based disconnections and cascade reactions in simplifying challenging syntheses.
  • The methodology provides access to unique terpenoid skeletons with potential applications in medicinal chemistry.