What question did this study set out to answer?

This research aims to develop synthesis methods for two grayanoids, (-)-mollfoliagein A and (-)-rhodomollein XXV.

April 15, 2026

Enantioselective Total Syntheses of Grayanoid (−)-Mollfoliagein A and (−)-Rhodomollein XXV

Key Points

This research aims to develop synthesis methods for two grayanoids, (-)-mollfoliagein A and (-)-rhodomollein XXV.
Conducted total syntheses using a convergent approach.
Employed a Stille carbonylative coupling for skeleton construction.
Implemented transannular oxa-Michael addition and vinylogous Knoevenagel condensation.
Reshaped bicyclo[3.3.0]octene to create bicyclo[3.2.1]octane system.
Used PPTS for functional conversion of (-)-mollfoliagein A to (-)-rhodomollein XXV.
Successfully synthesized (-)-mollfoliagein A with a characteristic 5/7/6/5/5 skeleton.
Formed C/D rings through a novel reshaping process.
Converted the synthesized compound to (-)-rhodomollein XXV with high efficiency.

Abstract

Herein, we report the convergent total syntheses of (-)-mollfoliagein A and (-)-rhodomollein XXV, two highly oxygenated grayanoids featuring a synthetically challenging oxa-tricyclo3.3.1.03.7nonane 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 bicyclo3.3.0octene unit to the highly functional bicyclo3.2.1octane ring system and PPTS mediated procedure for converting (-)-mollfoliagein A to (-)-rhodomollein XXV.

Connected Papers

Building similarity graph...

Analyzing shared references across papers

Discussion

Authors

Shu-Fei Du

Yipeng Zhang

Quan-Lin Wu

Journals

Journal of the American Chemical Society

Actions

Institutions

Yunnan University

References and Citations

Connected Papers

Building similarity graph...

Analyzing shared references across papers

Enantioselective Total Syntheses of Grayanoid (−)-Mollfoliagein A and (−)-Rhodomollein XXV

Key Points

Abstract

Citation Network

Connected Papers

Discussion

Authors

Journals

Actions

Institutions

References and Citations

Citation Network

Connected Papers

Discussion

Cite this study