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

Caroline G Webster; Hyeri Park; Amanda F Ennis; Jiyong Hong

doi:10.1016/j.tetlet.2021.153055

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

Tetrahedron Lett. 2021 May 11:71:153055. doi: 10.1016/j.tetlet.2021.153055. Epub 2021 Apr 6.

Authors

Caroline G Webster^#¹, Hyeri Park^#¹, Amanda F Ennis¹, Jiyong Hong¹

Affiliation

¹ Department of Chemistry, Duke University, Durham, North Carolina 27708, United States.

^# Contributed equally.

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.

Keywords: Antinociceptive activity; Bicyclo[3.2.1]octane; Grayanane diterpenoid; Radical cyclization; Rhodojaponin.

Abstract

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