Syntheses of Structurally Complex Marine Cyclopropyl‐Diterpenoids: Peyssonnoside A and Its Aglycon
Year: 2025
Type: article
Abstract: Peyssonnoside A is a marine-derived sulfated diterpenoid glucoside featuring a remarkable 5/6/3/6 tetracyclic skeleton with a highly substituted cyclopropane ring deeply embedded in its structure. Herein, we report on the full development of the first total synthesis of this natural product and its aglycon, peyssonnosol. Through the experimental evaluation of a series of synthetic strategies, including utilization of Ohloff-Rautenstrauch cycloisomerization and C-H allylation, we identified a concise, efficient, and highly diastereoselective route. Key steps in the synthesis of the aglycone peyssonnosol include a Simmons-Smith cyclopropanation and a Mukaiyama hydration, both guided by the inherent spatial features of the substrates. This optimized approach enabled the synthesis of peyssonnosol in 12 steps and 21 % overall yield and provides a robust framework for accessing structurally complex marine natural products.
Source: Chemistry - A European Journal
Authors: Gleb A. Chesnokov, Marco Schellenberg, Kevin Keller, Anthony Linden, Karl Gademann
Institution: University of Zurich
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,640
Funder: Universität Zürich
OpenAlex ID: W4408161947