Enantioselective Total Syntheses of Grayanoid (−)-Mollfoliagein A and (−)-Rhodomollein XXV
Abstract
Herein, we report the convergent total syntheses of (−)-mollfoliagein A and (−)-rhodomollein XXV, two highly oxygenated grayanoids featuring a synthetically challenging oxa-tricyclo[3.3.1.0 3.7 ]nonane structure unit. The characteristic 5/7/6/5/5 skeleton of mollfoliagein A was constructed in a single step from two fragments via a Stille carbonylative coupling/transannular oxa-Michael addition/vinylogous Knoevenagel condensation cascade. Other salient features are the C/D ring formation by reshaping the bicyclo[3.3.0]octene unit to the highly functional bicyclo[3.2.1]octane ring system and PPTS mediated procedure for converting (−)-mollfoliagein A to (−)-rhodomollein XXV.
Fields of Study & Subjects
Plant-derived Lignans Synthesis and Bioactivity
Bioactive Natural Diterpenoids Research
Chemical synthesis and alkaloids
Publication details
- Journal / source
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Volume
- 148
- Issue
- 15
- Pages
- 15410–15416
- Publication date
- 13 April 2026
- Language
- EN