Elaboration of an Intermolecular Diels-Alder Adduct En Route to the Spiro-Fused Oroidin Alkaloids

Authors

• Brandon Fulton, The University of Texas at Arlington
• Rasika Dias, The University of Texas at Arlington
• Delphine Gout, The University of Texas at Arlington
• Carl J. Lovely, Mississippi State University

ORCID

Lovely: https://orcid.org/0000-0001-7012-2001

MSU Affiliation

College of Arts and Sciences; Department of Chemistry

Creation Date

2026-06-30

Abstract

The dimeric oroidin alkaloids, exemplified by palau'amine, axinellamine, and massadine, remain challenging targets in the context of total synthesis owing to their compact and heteroatom-rich frameworks. A cycloaddition-rearrangement sequence has been developed using vinylimidazoles as substrates. The initial Diels-Alder adduct derived from urocanic acid and N-phenylmaleimide can be transformed into a lactone via a fluoride-induced ring-opening sequence. A twofold oxidation manifold affords the fully functionalized cyclopentane moiety present in palau'amine and congeners. Initial explorations to incorporate a second imidazole moiety are described.

Publication Date

7-30-2025

Publication Title

Synlett

Publisher

Thieme Gruppe

First Page

3064

Last Page

3070

Rights

© 2025 Thieme. All rights reserved.

Recommended Citation

Fulton, B., Dias, R., Gout, D., & Lovely, C. J. (2025). Elaboration of an Intermolecular Diels–Alder Adduct En Route to the Spiro-Fused Oroidin Alkaloids. Synlett, 36(18), 3064–3070. https://doi.org/10.1055/a-2644-2641