Enantioselective Total Synthesis of (–)‐Psiguadial A
Abstract
Abstract 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.
Article Details
Authors (9)
Liam P. O'Grady
Department of Chemistry & Biochemistry University of Delaware 163 The Green Newark Delaware 19716 USA
Marcel Achtenhagen
Department of Chemistry & Biochemistry University of Delaware 163 The Green Newark Delaware 19716 USA
Michael F. Wisthoff
Department of Chemistry & Biochemistry University of Delaware 163 The Green Newark Delaware 19716 USA
Robert S. Lewis
Department of Chemistry & Biochemistry University of Delaware 163 The Green Newark Delaware 19716 USA
Katarina Pfeifer
Weifeng Zheng
Department of Chemistry & Biochemistry University of Delaware 163 The Green Newark Delaware 19716 USA
Maxwell I. Martin
Department of Chemistry & Biochemistry University of Delaware 163 The Green Newark Delaware 19716 USA
Glenn P. A. Yap
Department of Chemistry and Biochemistry
William J. Chain
Department of Chemistry & Biochemistry University of Delaware 163 The Green Newark Delaware 19716 USA