Total syntheses of spiroviolene and spirograterpene A: a structural reassignment with biosynthetic implications.

ABSTRACT: The recent natural product isolates spiroviolene and spirograterpene A are two relatively non-functionalized linear triquinane terpenes with a large number of structural homologies. Nevertheless, three significant areas of structural disparity exist based on their original assignments, one of which implies a key stereochemical divergence early in their respective biosyntheses. Herein, using two known bicyclic ketone intermediates, a core Pd-catalyzed Heck cyclization sequence, and several chemoselective transformations, we describe concise total syntheses of both natural product targets and propose that the structure of spiroviolene should be reassigned. As a result, these natural products possess greater homology than previously anticipated.

SUBMITTER: Chi HM 

PROVIDER: S-EPMC8162393 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature