Publication: Concise Total Synthesis of Peyssonnoside A
Concise Total Synthesis of Peyssonnoside A
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Chesnokov, G. A., & Gademann, K. (2021). Concise Total Synthesis of Peyssonnoside A. Journal of the American Chemical Society, 143, 14083–14088. https://doi.org/10.1021/jacs.1c07135
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Peyssonnoside A is a marine-derived sulfated diterpenoid glucoside with a unique 5/6/3/6 tetracyclic skeleton with a highly substituted cyclopropane ring deeply embedded into the structure. Herein, we report the first total synthesis of this natural product in a concise, efficient, scalable, and highly diastereoselective fashion. The aglucone peyssonnosol was synthesized in 21% overall yield after 15 steps, featuring a Simmons–Smith cyclopropanation and Mukaiyama hydration, fully controlled by the spatial structure of the substrates.
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- Chesnokov, Gleb A
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Chesnokov, G. A., & Gademann, K. (2021). Concise Total Synthesis of Peyssonnoside A. Journal of the American Chemical Society, 143, 14083–14088. https://doi.org/10.1021/jacs.1c07135
