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.

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Cite This Study

Du et al. (Mon,) studied this question.

synapsesocial.com/papers/69df2c62e4eeef8a2a6b17cb https://doi.org/https://doi.org/10.1021/jacs.6c03596

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