title: Exploration of an epoxidation-ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, Brigham Young University, C100 BNSN, Provo, UT, 84602, USA.
authors.forename: Brad M
authors.initials: BM
authors.lastname: Loertscher
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.forename: Steven L
authors.initials: SL
authors.lastname: Castle
keywords: Lewis acid; Myers alkylation; Payne rearrangement; Shi epoxidation; lyconadin A