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

21 Scopus citations

Abstract

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
Volume54
Issue number38
DOIs
StatePublished - Sep 14 2015

Bibliographical note

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

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

Fingerprint

Dive into the research topics of 'A Divergent Enantioselective Strategy for the Synthesis of Griseusins'. Together they form a unique fingerprint.

Cite this