Total Synthesis of Isoriccardin C and Isoriccardin D Based on a Hydroxyl-Directed Palladium-Catalyzed Intramolecular C–H Alkenylation

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2026_organic_gulias_total.pdf (2.09 MB)
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URI: https://hdl.handle.net/10347/47246
ISSN: 4836–4840
DOI: 10.1021/acs.orglett.6c00911

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2026-04-06

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American Chemical Society
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Abstract

A concise, nine-step total synthesis of isoriccardin C and isoriccardin D has been developed. The strategy centers on the sequential installation of the four aromatic rings of the backbone by using three key transformations: Suzuki coupling, Wittig olefination, and Ullmann coupling. The pivotal step is a palladium(II)-catalyzed, intramolecular ortho-alkenylation that forges the 18-membered macrocyclic core. This streamlined route enables the total synthesis with minimal reliance on protecting groups, and its modular nature offers a versatile platform for the construction of structural analogues.

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Chemical synthesis| Hydrocarbons| Macrocyclization| Olefination| Organic synthesis

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Losada, P., Mascareñas, J. L., & Gulías, M. (2026). Total Synthesis of Isoriccardin C and Isoriccardin D Based on a Hydroxyl-Directed Palladium-Catalyzed Intramolecular C-H Alkenylation. "Organic letters", 28(15), 4836-4840. https://doi.org/10.1021/ACS.ORGLETT.6C00911

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This work received financial support from the Spanish Government (Grants PID2022-137318OB-I00 and PID2022-136785NB-I00 funded by MCIN/AEI/10.13039/501100011033, Grant IHRC22-00009 funded by MCIN/ISCIII and the “European Union Next Generation EU/PRTR” and ORFEO–CINQA network RED2022-134287-T) and “ERDF A way of making Europe”. The authors also thank the Xunta de Galicia (Grants ED431C 2021/25, ED431C 2025/02, and ED431G 2023/03: Centro Singular de Investigación de Galicia accreditation 2023–2027. and predoctoral fellowship to P.L.) and the European Union (European Regional Development Fund-ERDF corresponding to the multiannual financial framework 2014–2020).

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Copyright © 2026 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0 .
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Química Orgánica
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