Total Synthesis of Methyl 1,5,8-Trimethoxy-1H-isochromene-3-carboxylate and Its Derivatives via Palladium-Catalyzed Annulation of 2-Alkynylbenzaldehydes

Nolan Nardangeli; Jared Thomson; Nikola Topolovčan; Tomáš Hudlický

doi:10.1055/a-1532-8656

Synthesis, Table of Contents

Synthesis 2021; 53(21): 4110-4116
DOI: 10.1055/a-1532-8656

paper

Total Synthesis of Methyl 1,5,8-Trimethoxy-1H-isochromene-3-carboxylate and Its Derivatives via Palladium-Catalyzed Annulation of 2-Alkynylbenzaldehydes

Nolan Nardangeli

^aDepartment of Chemistry and Centre for Biotechnology, Brock University, 1812 Sir Isaac Brock Way, St. Catharines, Ontario L2S 3A1, Canada

,

Jared Thomson

^aDepartment of Chemistry and Centre for Biotechnology, Brock University, 1812 Sir Isaac Brock Way, St. Catharines, Ontario L2S 3A1, Canada

,

Nikola Topolovčan ∗

^bLaboratory for Biomimetic Chemistry, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10 000 Zagreb, Croatia

,

Tomáš Hudlický ∗

^aDepartment of Chemistry and Centre for Biotechnology, Brock University, 1812 Sir Isaac Brock Way, St. Catharines, Ontario L2S 3A1, Canada

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Abstract

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Abstract

A 7-step total synthesis of methyl 1,5,8-trimethoxy-1H-isochromene-3-carboxylate and a 5-step synthesis of its C-3 derivatives are reported. Sonogashira coupling of 2-halobenzaldehydes with terminal acetylenes was employed to access 2-alkynylbenzaldehydes, which underwent a Pd-catalyzed annulation to afford the corresponding isochromene-containing products.

Key words

2-alkynylbenzaldehydes - antitumor agents - isochromene annulations - palladium catalysis - total synthesis

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References

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