Tetrahedron p. 3879 - 3916 (1997)
Update date:2022-08-02
Topics:
Pelter, Andrew
Hussain, Amjad
Smith, Gareth
Ward, Robert S.
(Z)-1-Hydroxy-3-(3'-hydroxyphenyl)prop-2-enes undergo phenolic oxidation by phenyliodonium diacetate (PIDA) in methanol to give 8a-methoxy-2H,6H-dihydrochromen-6-ones. These are reduced by DIBAL-H to 2-substituted-Δ3,4-chromenes the overall process being a unique heterocyclic synthesis in which the heteroatom is not initially attached to a benzene ring, but is introduced from a side chain. Parallel oxidations using cis-1-hydroxy-3-(3'-hydroxyphenyl)prop-2,3-oxiranes have also been achieved despite the presence of the sensitive oxirane ring.
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(1997)