Bioinspired Synthesis of Sceptrin, Ageliferin and Six Piperine Dimers by Photo(Flow) catalysis: [2+2] vs [4+2] Cycloaddition

09 June 2025, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We describe a unified, bioinspired total synthesis of eight dimeric natural products, including nigramide R, chabamide, dipiperamide F and G and the emblematic marine alkaloids sceptrin, dibromosceptrin, ageliferin and dibromoageliferin. Central to this approach is a photocatalytic dimerization of either piperine, or fully elaborated hymenidin- and oroidin-type precursors via catalyst-controlled [2+2] or [4+2] cycloadditions. Notably, this work constitutes the first total syntheses of sceptrin, ageliferin, dibromosceptrin, and dibromoageliferin achieved by direct assembly of the native hymenidin and oroidin frameworks. To overcome the limitations of prolonged photochemical exposure and photodegradation, we transitioned from traditional batch processing to low-cost, 3D-printed PhotoFlow reactors, enabling improved efficiency and scalability. Ultimately, this approach offers a general platform for the streamlined synthesis of dimeric marine alkaloids.

Keywords

Cycloadditions
Photocatalysis
Continuous Flow
3D Printed Reactors
Piperine
Sceptrin
Ageliferin

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