Enantioselective Total Synthesis of (–)‐Psiguadial A
The first enantioselective total synthesis of the antiproliferative natural product (-)-psiguadial A is reported. This approach features the enantioselective synthesis of a complex tricyclic terpenoid precursor, the union of that precursor with a polyketide component by an enolate-ortho-quinone methide coupling reaction to form a highly congested carbon─carbon bond, and an acid-mediated intramolecular hydration ring-closure leveraging a fully substituted alkene to generate the unique oxepane core structure of the natural product.
Authors
- Robert S. Lewis
- Glenn P. A. Yap (ORCID: https://orcid.org/0000-0003-0385-387X)
- William J. Chain (ORCID: https://orcid.org/0000-0003-0312-6250)
- Maxwell I. Martin (ORCID: https://orcid.org/0000-0002-0095-1282)
- Michael F. Wisthoff (ORCID: https://orcid.org/0000-0001-5597-1419)
- Wei‐Feng Zheng
- Liam P. O’Grady
- Marcel Achtenhagen
- Katarina Pfeifer (ORCID: https://orcid.org/0000-0001-9671-1234)
Institutions
- University of Delaware (US)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2025-05-20
- DOI
- https://doi.org/10.1002/anie.202506537
- Citations
- 2
- Primary Topic
- Synthesis of Indole Derivatives
- Type
- article
- Field-Weighted Citation Impact
- 1.87