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Haut, Franz-Lucas; Speck, Klaus; Wildermuth, Raphael; Möller, Kristof; Mayer, Peter; Magauer, Thomas (2018): A Negishi cross-coupling reaction enables the total synthesis of (+)-stachyflin. In: Tetrahedron, Vol. 74, No. 26: pp. 3348-3357
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We present a full account on the development of the total synthesis of the antiviral meroterpenoid (+)-stachyflin. The decalin subunit is rapidly accessed by an exo-selective Diels-Alder reaction, whereas the isonindolinone was synthesized via a highly efficient and practical de novo route starting from dimedone. A challenging sp(2)-sp(3) Negishi cross-coupling reaction enabled construction of the crucial C15-C16 bond that connects the arene with the decalin subunit. For the final installation of the cis-decalin framework, a Lewis acid-catalyzed cyclization was applied.