A Divergent Enantioselective Strategy for the Synthesis of Griseusins

Yinan Zhang, Qing Ye, Xiachang Wang, Qing Bai She, Jon S. Thorson

Research output: Contribution to journalArticlepeer-review

20 Scopus citations


The first enantioselective total synthesis of griseusin A, griseusin C, 4′-deacetyl-griseusin A, and two non-native counterparts in 11–14 steps is reported. This strategy highlights a key hydroxy-directed CH olefination of 1-methylene isochroman with an α,β-unsaturated ketone followed by subsequent stereoselective epoxidation and regioselective cyclization to afford the signature tetrahydro-spiropyran ring. Colorectal cancer cell cytotoxicities of the final products highlight the impact of the griseusin tetrahydro-spiropyran ring on bioactivity. As the first divergent enantioselective synthesis, the strategy put forth sets the stage for further griseusin mechanism-of-action and SAR studies.

Original languageEnglish
Pages (from-to)11219-11222
Number of pages4
JournalAngewandte Chemie - International Edition
Issue number38
StatePublished - Sep 14 2015

Bibliographical note

Funding Information:
This work was supported, in part, by the University of Kentucky College of Pharmacy, the University of Kentucky Markey Cancer Center, National Institutes of Health grant CA175105 (Q.‐B. She), and the National Center for Advancing Translational Sciences (UL1TR000117).

Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim


  • CH activation
  • aromatic polyketides
  • natural products
  • pyranonaphthoquinones
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)


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