DOI: 10.1002/ejoc.70620 ISSN: 1434-193X
Epoxidation of Cashmeran and Unprecedented Rearrangement to an α‐Carbonyl δ‐Spirolactone
Lukas Kell, Niklas Bartsch, Johannes Panten, Marcus Eh, Jan Paradies, Hans Egold, Anke Spannenberg, Thomas WernerWe report the epoxidation of Cashmeran followed by a domino Baeyer‐Villiger oxidation and a previously unrecognized acid‐catalyzed rearrangement, furnishing a novel α‐carbonyl δ‐spirolactone. Nuclear Magnetic Resonance (NMR) spectroscopic studies and single crystal X‐ray diffraction analysis confirmed the formation of the δ‐spirolactone. Furthermore, the proposed reaction mechanism was investigated by computational methods supporting a stereoselective transannular transesterification as key step in the formation of the novel δ‐spirolactone.