Overriding Stereochemical Outcomes in Cyclase Phase Total Synthesis: Enantioselective Synthesis of Habiterpenol and Dasyscyphin A
Abstract
High Resolution Image Download MS PowerPoint Slide Herein, we report the enantioselective total syntheses of habiterpenol and dasyscyphin A. By exploiting a quaternary carbon stereocenter epimerization protocol, we could override the intrinsic stereochemical bias of polyolefin cyclization reactions. Accordingly, we achieved the efficient and selective construction of the polycyclic scaffolds of both meroterpenoid natural products that bear an unconventional cis -hydrindane motif. This work demonstrates the utility of stereocenter remodeling in reprogramming the outcomes of biomimetic cyclizations, thus enabling the rapid synthesis of terpenoid frameworks that deviate from the prototypical all- trans -ring fusions.
Fields of Study & Subjects
Plant biochemistry and biosynthesis
Synthetic Organic Chemistry Methods
Sesquiterpenes and Asteraceae Studies
Publication details
- Journal / source
- Journal of the American Chemical Society
- Volume
- 148
- Issue
- 7
- Pages
- 6820–6825
- Publication date
- 11 February 2026
- Language
- EN