Total Synthesis of (+)- and (±)-Hosieine A

Yu-Wen Huang; Ke Kong; John L Wood

doi:10.1002/anie.201804076

Total Synthesis of (+)- and (±)-Hosieine A

Angew Chem Int Ed Engl. 2018 Jun 25;57(26):7664-7667. doi: 10.1002/anie.201804076. Epub 2018 May 25.

Authors

Yu-Wen Huang¹, Ke Kong¹, John L Wood¹

Affiliation

¹ Department of Chemistry and Biochemistry, Baylor University, One Bear Place 97348, Waco, TX, 76798, USA.

PMID: 29723446
DOI: 10.1002/anie.201804076

Abstract

Described herein is a concise total synthesis of the highly potent nicotinic acetylcholine receptor ligand hosieine A in racemic and enantioenriched forms. The synthesis requires only seven steps and features a telescoped reaction sequence initiated by a gold-catalyzed Rautenstrauch reaction.

Keywords: electrocyclization; enantioselectivity; gold; natural products; total synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Gold / chemistry
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry
Heterocyclic Compounds, 4 or More Rings / metabolism
Ligands
Molecular Structure
Receptors, Nicotinic / metabolism
Stereoisomerism

Substances

Heterocyclic Compounds, 4 or More Rings
Ligands
Receptors, Nicotinic
hosieine A
Gold