General Strategy Toward the Total Synthesis of Welwitindolinone Alkaloids & Atroposelective C-P Coupling: Asymmetric Synthesis of QUINAP Ligands

Seminar series
Organic Colloquium
When
Mon, May 13 5:00pm
Where
Cram Conference Room - 3440 Molecular Sciences Bldg
Speaker Dr. Vikram Bhat
California Institute of Technology
Division of Chemistry and Chemical Engineering
Description

Special Organic Seminar

"General Strategy Toward the Total Synthesis of Welwitindolinone Alkaloids & Atroposelective C-P Coupling: Asymmetric Synthesis of QUINAP Ligands"

Abstract

Part 1. The welwitindolinones are densely functionalized alkaloids that possess interesting biological activity. Our synthetic endeavors resulted in the total synthesis of several members and analogues of this fascinating natural product family. The key features of the synthesis include a Pd-catalyzed enolate arylation reaction to construct the welwitindolinone framework, and a one-pot aldoxime to isothiocyanate rearrangement.

Part 2. Using high-throughput approach, a novel atroposelective C-P coupling has been developed. This methodology was used in the asymmetric synthesis of QUINAP and related P,N ligands via kinetic resolution of readily accessible precursors.

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