A. Pelter, A. Hussain, Gareth R. Smith
Mar 17, 1997
Citations
0
Influential Citations
29
Citations
Journal
Tetrahedron
Abstract
Abstract (Z)-1-Hydroxy-3-(3′-hydroxyphenyl)prop-2-enes undergo phenolic oxidation by phenyliodonium diacetate (PIDA) in methanol to give 8a-methoxy-2 H ,6 H -dihydrochromen-6-ones. These are reduced by DIBAL-H to 2-substituted- Δ 3,4 -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 - l -hydroxy-3-(3′-hydroxyphenyl)prop-2,3-oxiranes have also been achieved despite the presence of the sensitive oxirane ring.