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Updated: Feb 5, 2026

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Total Syntheses of Aromatic Abietane Diterpenoids Utilizing Advances in the Pummerer Rearrangement
1Department of Chemistry , Oregon State University , Corvallis , Oregon 97331 , United States.
Abstract:
The first total syntheses of triptobenzene T, vitexifolin C, 4- epi-triptobenzene L, triptobenzene L, and nepetaefolin F have been accomplished through an enantioselective, common intermediate approach and have enabled the confirmation and/or establishment of the absolute stereochemistry of each natural product synthesized. Application of three new and/or underutilized Pummerer reaction pathways proved critical to the synthetic work. A proline sulfonamide-catalyzed Yamada-Otani reaction was used to access the highly functionalized cyclohexane A ring core, including the C10 all-carbon quaternary stereocenter. Additionally, the importance of the A ring unsaturation for controlling the stereoselectivity during the C4 alkylation is showcased.
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