Journal
SYNLETT
Volume 32, Issue 12, Pages 1187-1191Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1527-3781
Keywords
Diels-Alder reaction; regioselectivity; ring cleavage; tetrahydroisobenzofuran; viridin; furanosteroids
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Funding
- JSPS KAKENHI [18HO4411, 18H02556]
- Platform Project for Supporting Drug Discovery and Life Science Research [Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)] from AMED [JP21am0101084]
- Grants-in-Aid for Scientific Research [18H02556] Funding Source: KAKEN
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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.
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.
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