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Synthesis 2021; 53(21): 4110-4116
DOI: 10.1055/a-1532-8656
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
We are grateful to the following agencies for financial support of this work: the Natural Sciences and Engineering Research Council of Canada (NSERC; Idea to Innovation and Discovery Grants), the Canada Research Chair Program, the Canada Foundation for Innovation (CFI), TDC Research, Inc., the TDC Research Foundation, the Ontario Partnership for Innovation and Commercialization (OPIC), and The Advanced Biomanufacturing Centre (Brock University).
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 synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1532-8656.
- Supporting Information
Publication History
Received: 30 April 2021
Accepted after revision: 21 June 2021
Accepted Manuscript online:
21 June 2021
Article published online:
27 July 2021
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