Synthetic Efforts Toward the Bicyclo[3.2.1]octane Fragment of Rhodojaponin III

Overview

Journal Tetrahedron Lett

Publisher Elsevier

Specialty Chemistry

Date 2021 May 31

PMID 34054153

Citations 1

Authors

Caroline G Webster

Hyeri Park

Amanda F Ennis

Jiyong Hong

Affiliations

Soon will be listed here.

Abstract

Rhodojaponin III is a grayanane-type diterpenoid natural product with a novel chemical scaffold. It shows potent antinociceptive activity and may represent a new class of natural non-opioid analgesics with a novel mode of action. We explored the Au(I)-catalyzed Conia-ene cyclization and the Mn(III)-mediated radical cyclization of alkynyl ketones for the synthesis of the bicyclo[3.2.1]octane fragment of rhodojaponin III. These strategies will be applicable in the synthesis of rhodojaponin III and analogs for future biological studies.

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.

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