Pd‐Catalyzed Regio‐ and Diastereoselective Heck Cyclization to Access Bicyclo[3.2.1]octanone Ring Systems

Bridged‐ring systems, especially the bicyclo[3.2.1]octanes, are widely found as key structural motifs in 6,7‐seco‐ent‐kaurane diterpenoids. In an effort directed towards the total synthesis of sculponeatin N, a Pd‐catalyzed regioselective reductive‐Heck cyclization was developed to access variously substituted bicyclo[3.2.1]octan‐2‐ones, with isolated yields up to 94 %, starting from commercially available anisole derivatives. The reactions displayed complementary merits to classical radical‐mediated pathway in both avoiding stoichiometric tin reagent and good compatibility towards alkyne/alkene bearing substrates.

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