Journal article
The role of the oxygen atom in benzylic hydroxylations of naphthopyrans
South African Journal of Chemistry, Vol.43(3-4), pp.96-100
1990
Abstract
Benzylic hydroxylation of 5,1 0-dimethoxy-2,2-dimethylnaphtho[2,3-bj pyran followed by oxidative demethylation afforded the naturally occurring 4-hydroxy-a-lapachone as its racemate, in 72% yield. Treatment of trans-1 ,2,3,4-tetrahydro-5, 1 0-dimethoxy-1 ,3-dimethylanthracene under similar conditions failed to hydroxylate the 4-position. It would thus appear that the naphthopyran ring-oxygen facilitates benzylic hydroxylations at C(4) in both naphtho[2,3-bj- and naphtho[2,3-cJpyrans.
Details
- Title
- The role of the oxygen atom in benzylic hydroxylations of naphthopyrans
- Authors/Creators
- R.G.F. Giles (Author/Creator)I.R. Green (Author/Creator)
- Publication Details
- South African Journal of Chemistry, Vol.43(3-4), pp.96-100
- Publisher
- South African Bureau for Scientific Publications
- Identifiers
- 991005540410607891
- Copyright
- © 1990 South African Chemical Institute (SACI)
- Murdoch Affiliation
- Murdoch University
- Language
- English
- Resource Type
- Journal article
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