3. A Negishi cross-coupling reaction enables the total synthesis of (+)-stachyflin
F.-L. Haut, K. Speck, R. Wildermuth, K. Möller, P. Mayer, T. Magauer*
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 sp2–sp3 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.
Title
3. A Negishi cross-coupling reaction enables the total synthesis of (+)-stachyflin
Author
F.-L. Haut, K. Speck, R. Wildermuth, K. Möller, P. Mayer, T. Magauer*
Citation
Tetrahedron 2018, 74, 3348–3357
Type
Text