Synthetic Studies on the Viridin Skeleton through Regio- and Stereoselective Functionalization of the AE-Ring Moiety

Abstract 4,5,6,7-Tetrahydroisobenzofurans, corresponding to the AC(D)E ring structure of viridin and equipped with required substituents on the A-ring, were synthesized with high regio- and stereoselectivities via the Diels–Alder adduct of a furan derivative and maleic anhydride. The key steps of th...

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Bibliographic Details
Published in:Synlett 2021-07, Vol.32 (12), p.1187-1191
Main Authors: Hori, Shuhei, Ishida, Sho, Itoh, Go, Sugiyama, Koji, Yuki, Chiharu, Egi, Masahiro, Yahata, Kenzo, Ikawa, Takashi, Akai, Shuji
Format: Article
Language:English
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Summary:Abstract 4,5,6,7-Tetrahydroisobenzofurans, corresponding to the AC(D)E ring structure of viridin and equipped with required substituents on the A-ring, were synthesized with high regio- and stereoselectivities via the Diels–Alder adduct of a furan derivative and maleic anhydride. The key steps of this work include the regioselective opening of a tetrahydrofuran ring, a stereoselective epoxidation, and an AlMe 3 -mediated regioselective epoxide opening followed by stereoselective C-methylation.
ISSN:0936-5214
1437-2096
DOI:10.1055/a-1527-3781