Abstract
Vitamin‐B12‐Catalyzed C, C‐Bond Formation: Synthesis of Jasmonates via Sequential Radical ReactionThe Cbl‐catalyzed electroreduction of 3‐(2′‐bromo‐1′‐ethoxyethoxy)cyclopenten (1a) in presence of 1‐cyanovinyl‐acetate (8) gave, in a sequential radical reaction (5‐exo‐trig‐cyclization of 1a followed by addition to 8), 1‐cyano‐2‐(2′‐ethoxy‐hexahydro‐2′H‐cyclopenta[b] furan‐4′‐yl)ethyl acetate (10a). This intermediate was transformed to methyl jasmonate (7; four steps) and epituberolide (9; three steps) in 20 and 31% yield, respectively, from cyclopent‐2‐en‐l‐ol.
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