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.
Supplementary materials
Title
Eudesmane Supporting Information
Description
Optimization tables, Experimental Procedures, Details of X-ray Analyses, and NMR Spectra
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Title
Crystal Structure Data
Description
CCDC Nos. 2283606, 2283607, 2283609, 2283610, 2283611, 2283612, 2283613, 2283614, 2283662,
and 2283664
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