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.

SUBMITTER: Loertscher BM 

PROVIDER: S-EPMC3701374 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature