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

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 AlMe3-mediated regioselective epoxide opening followed by stereoselective C-methylation.

Automated summary

4,5,6,7-Tetrahydroisobenzofurans, corresponding to the AC(D)E ring structure of viridin with required substituents on the A-ring, were synthesized via Diels-Alder adduct of a furan derivative and maleic anhydride with high regio- and stereoselectivities. Key steps in this synthesis included regioselective ring opening, stereoselective epoxidation, and AlMe3-mediated regioselective epoxide opening followed by stereoselective C-methylation.