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

ABSTRACT: 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.

SUBMITTER: Lopez-Mendoza P

PROVIDER: S-EPMC10729057 | biostudies-literature | 2023 Dec

REPOSITORIES: biostudies-literature

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

López-Mendoza Pedro P Porras-Santos Luis F LF Pérez-Bautista José Alvano JA Quintero Leticia L Bautista-Nava Jocelyn J León-Rayo David F DF Cordero-Vargas Alejandro A Sartillo-Piscil Fernando F

The Journal of organic chemistry 20231204 24

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 oxidat ...[more]

PMID: 38049195

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