Streamlined Synthesis of Eudesmane Sesquiterpenoids through Site-switchable Olefin Functionalization Strategy

30 May 2024, Version 3
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Herein, we demonstrate a concise synthesis of oxidized eudesmanes using a late-stage site-selective olefin functionalization strategy. To implement this strategy, we synthesized a common intermediate comprising two identical olefins within a hydroxy-carrying eudesmane core via an asymmetric tandem Michael addition and Aldol reaction, along with an Au(I)-catalyzed Alder-ene reaction. Subsequent late-stage site-selective olefin hydrogenation and epoxidation techniques were employed to synthesize nine eudesmane congeners without using protecting groups. This study highlights the applicability and effectiveness site-selective functionalization of identical olefins in facilitating the access to intricate terpenes and their derivatives.

Keywords

Natural Product Synthesis
sesquiterpenes
Gold catalysis
site-selective functionalization
epoxidation

Supplementary materials

Title
Description
Actions
Title
Eudesmane Supporting Information
Description
Optimization tables, Experimental Procedures, Details of X-ray Analyses, and NMR Spectra
Actions

Supplementary weblinks

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