TY - JOUR A1 - Loertscher, Brad M. A1 - Zhang, Yu A1 - Castle, Steven L. T1 - Exploration of an epoxidation–ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement JF - Beilstein Journal of Organic Chemistry PY - 2013/// VL - 9 SP - 1179 EP - 1184 SN - 1860-5397 DO - 10.3762/bjoc.9.132 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.9.132 KW - Lewis acid KW - lyconadin A KW - Myers alkylation KW - Payne rearrangement KW - Shi epoxidation N2 - In the context of synthetic efforts targeting the alkaloid lyconadin A, scalemic epoxide 25 was prepared by a highly stereoselective sequence involving a Myers alkylation and a Shi epoxidation. Ring-opening of this epoxide with a vinylcopper complex afforded alcohol 26 instead of the expected product 27. An unusual Lewis acid promoted Payne rearrangement of an α-trityloxy epoxide is proposed to account for this outcome. ER -