Efficient Total Synthesis of Three Alpinoids Via the Au(I)-catalyzed Meyer-Schuster Rearrangement

Overview

Journal Tetrahedron Lett

Publisher Elsevier

Specialty Chemistry

Date 2024 Apr 8

PMID 38584726

Authors

Jasmine K Keyes

Mauri B Butzke

Kenneth A Miller

Affiliations

Soon will be listed here.

Abstract

The total syntheses of three structurally related natural products, deoxyalpinoid B, deoxyalpinoid A, and alpinoid F, are reported, and each features a Au(I)-catalyzed Meyer-Schuster rearrangement as the key step. The synthesis of alpinoid F is reported for the first time. The syntheses of these natural products, all of which exhibit potent anticancer activity, are readily amenable to the preparation of structural analogs.

Citing Articles

Improved synthesis of deoxyalpinoid B and quantification of antileishmanial activity of deoxyalpinoid B and sulforaphane.

Leary E, Anderson E, Keyes J, Huskie T, Blake D, Miller K Bioorg Med Chem. 2022; 78:117136.

PMID: 36565668 PMC: 9903332. DOI: 10.1016/j.bmc.2022.117136.

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