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Updated: May 25, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Synthesis of Daucane Natural Products Enabled by a Gold(I)-Catalyzed Tandem Cycloisomerization/(4 + 3) Cycloaddition
Àlex Martí1,2, Helena Armengol-Relats1,2, Anna Sadurní1
1Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology (BIST), Av. Països Catalans 16, 43007 Tarragona, Spain.
Abstract:
A divergent synthesis of three members of the daucane family of natural products is reported, enabled by a gold(I)-catalyzed cycloisomerization/formal (4 + 3) cycloaddition as the key step. The synthesis of penigrisacid A features a vanadium-catalyzed tandem epoxidation/SN2' cyclization, whereas a Suárez radical cyclization enables the synthesis of aspterric acid. This work has also led to the reassignment of the structure of penigrisacid A as well as a short formal synthesis of schisanwilsonene A.
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