Gold-catalyzed Synthesis of Carbon-bridged Medium-sized Rings

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2009 Sep 11

PMID 19739690

Citations 16

Authors

Francis Barabe

Genevieve Betournay

Gabriel Bellavance

Louis Barriault

Affiliations

Soon will be listed here.

Abstract

Bicyclo[m.n.1]alkenone frameworks possessing quaternary carbon centers adjacent to a bridged ketone are frequently found in bioactive natural products. Although several methods have been developed to construct such frameworks, most of them are specific to a particular scaffold. Herein, we report a mild and highly efficient method to generate carbon-bridged frameworks of various sizes using phosphino gold(I) catalysts.

Citing Articles

Total synthesis of grayanane natural products.

Fay N, Blieck R, Kouklovsky C, de la Torre A Beilstein J Org Chem. 2022; 18:1707-1719.

PMID: 36570567 PMC: 9764858. DOI: 10.3762/bjoc.18.181.

Concise and Stereoselective Total Syntheses of Annotinolides C, D, and E.

Qu P, Snyder S J Am Chem Soc. 2021; 143(31):11951-11956.

PMID: 34338524 PMC: 8397315. DOI: 10.1021/jacs.1c05942.

Synthetic efforts toward the bicyclo[3.2.1]octane fragment of rhodojaponin III.

Webster C, Park H, Ennis A, Hong J Tetrahedron Lett. 2021; 71.

PMID: 34054153 PMC: 8153367. DOI: 10.1016/j.tetlet.2021.153055.

A Catalytic Intermolecular Formal Ene Reaction between Ketone-Derived Silyl Enol Ethers and Alkynes.

Holmbo S, Godfrey N, Hirner J, Pronin S J Am Chem Soc. 2016; 138(38):12316-9.

PMID: 27626462 PMC: 6791363. DOI: 10.1021/jacs.6b06847.

Stereoselective Halogenation in Natural Product Synthesis.

Chung W, Vanderwal C Angew Chem Int Ed Engl. 2016; 55(14):4396-434.

PMID: 26833878 PMC: 6028003. DOI: 10.1002/anie.201506388.