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DOI: 10.1055/a-2644-2641
Elaboration of an Intermolecular Diels–Alder Adduct En Route to the Spiro-Fused Oroidin Alkaloids
This work has been supported by the Robert A. Welch Foundation (Y-1362). We are grateful to the NSF for instrumentation grants (CHE-0234811 and CHE-084059) to acquire the NMR spectrometers used in this research.
Supported by: National Science Foundation CHE0234811, CHE0840509
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 History
Received: 29 April 2025
Accepted after revision: 26 June 2025
Article published online:
30 July 2025
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