En Route to Furan-Fused Naphthopyrones: Formal Synthesis of the (+)-Lasionectrin and Its C12-Epimer

En Route to Furan-Fused Naphthopyrones: Formal Synthesis of the (+)-Lasionectrin and Its C12-Epimer

Despite the vast presence of the furan-fused naphthopyrone (FFN) skeleton in many bioactive natural products, such as lasionectrin, at present, a general approach to FFNs has not been developed yet. For that reason, a simple and straightforward synthetic approach consisting of a sequential procedure...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 88; no. 24; pp. 17409 - 17419
Main Authors: López-Mendoza, Pedro, Porras-Santos, Luis F., Pérez-Bautista, José Alvano, Quintero, Leticia, Bautista-Nava, Jocelyn, León-Rayo, David F., Cordero-Vargas, Alejandro, Sartillo-Piscil, Fernando
Format: Journal Article
Language:English
Published: United States American Chemical Society 15-12-2023
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Summary:Despite the vast presence of the furan-fused naphthopyrone (FFN) skeleton in many bioactive natural products, such as lasionectrin, at present, a general approach to FFNs has not been developed yet. For that reason, a simple and straightforward synthetic approach consisting of a sequential procedure of a Diels–Alder reaction between 1,3-dimethoxy-benzocyclobutenol I and furan-fused-α,β-unsaturated-δ-lactones II (via an ο-quinodimethane intermediate III) followed by an oxidative aromatization of the corresponding Diels–Alder adduct IV is reported. Subsequently, the formal synthesis of the (+)-lasionectrin and its C12-epimer was achieved, the latter in only six steps.
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02231