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Asymmetric Total Synthesis of (+)-Verrubenzospirolactone and (+)-Capillobenzopyranol.

Dattatraya H DetheSakshi JuyalNitin SharmaUtpal Kundu
Published in: Organic letters (2024)
The first asymmetric total synthesis of (+)-verrubenzospirolactone ( 1 ), a distinctive highly fused benzosesquiterpenoid, characterized by a pentacyclic skeletal structure, is realized through a concise 10-step synthetic pathway with an impressive 22.8% overall yield. Notable highlights of this synthetic endeavor include (i) the introduction of a Ru-catalyzed ortho C-H activation step, (ii) the application of Pd-catalyzed asymmetric allylic alkylation to establish a pivotal stereocenter at C-3 with an excellent enantiomeric excess, (iii) B -alkyl Suzuki-Miyaura coupling to construct a Diels-Alder precursor, and, ultimately, (iv) the successful deployment of an intramolecular Diels-Alder reaction to complete the synthesis of (+)-verrubenzospirolactone without erosion of the enantiomeric excess.
Keyphrases
  • room temperature
  • solid state
  • ionic liquid
  • capillary electrophoresis
  • energy transfer
  • mass spectrometry
  • electron transfer