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Updated: Jul 12, 2026

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
A General Approach to geminal-Dimethyl trans-Decalin Terpenoids
Eric L Pettipiece1, Sabnam Begum1, Julio Cacho Bravo1
1Department of Chemistry, Rice University, Houston, Texas 77005, United States.
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Terpenoid natural products exhibit remarkable structural diversity and complexity, characterized by intricate carbon scaffolds and interesting oxidation patterns. However, there exist common core motifs found in thousands of natural products that represent key targets for synthesis. One such example is the trans-decalin bearing C(4) geminal-dimethyl substitution. Traditionally accessed from the Wieland-Miescher ketone or through polyene cyclization, new methods for rapid access to C(4) dimethyl trans-decalins are of great interest. Herein, we report the realization of a palladium-catalyzed reductive Heck reaction that provides robust and scalable entry to three key building blocks in three steps from (R)-(nor)carvone. The utility of the resulting products is demonstrated through the total synthesis of 10 terpenoid natural products from three distinct families.
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