Towards an efficient methodology for the synthesis of functionalized dihydropyrans by silyl-Prins cyclization: access to truncated natural products.

ABSTRACT: We herein present a selective methodology for the synthesis of disubstituted dihydropyrans by silyl-Prins cyclization of Z-vinylsilyl alcohols mediated by trimethylsilyl trifluoromethanesulfonate (TMSOTf). The reaction features broad substrate scope, short reaction times and ease of process scale-up. Moreover, to showcase the applicability of the proposed method, we also report a facile and linear synthesis of analogues of rhopaloic acid and natural doremox fragrance.

SUBMITTER: Pena LF 

PROVIDER: S-EPMC10762716 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature