Journal article
The stereoselective formation of naphtho[1,2-c]pyrans, angular analogues of the aphin-derived glucoside B, by an intramolecular version of the Mukaiyama reaction of 4-naphthyldioxolanes
Journal of the Chemical Society, Perkin Transactions 1, (7), pp.865-873
1994
Abstract
Stereoselective isomerisation of the pair of epimers rel-(2R,4S,5S)- and rel-(2S,4S,5S)-4-(4-isopropoxy-5,7-dimethoxynaphthalene-2-yl)-2,5-dimethyl dioxolane 12 with an excess of a mixture of titanium tetrachloride and titanium tetraisopropoxide afforded the two products rel-(1R,3S,4S)-3,4-dihydro-4-hydroxy-6-isopropoxy-7,9-dimethoxy-1,3-dimethylnaphtho[1,2-c]pyran 13, and the C-1 epimer 15. Isomerisation of rel-(2S,4R,5S)-4-(8-bromo-4-isopropoxy-5,7-dimethoxynaphthalen-2-yl)-2,5-dimethyl dioxolane 36 with an excess of titanium tetrachloride alone afforded rel-(1S,3S,4R)3,4-dihydro-4-hydroxy-6-isopropoxy-7,9-dimethoxy-1,3-dimethylnaphtho[1,2-c]pyran 38 and its 5-bromo derivative 39, the latter being formed through bromine migration on the aromatic nucleus.
Details
- Title
- The stereoselective formation of naphtho[1,2-c]pyrans, angular analogues of the aphin-derived glucoside B, by an intramolecular version of the Mukaiyama reaction of 4-naphthyldioxolanes
- Authors/Creators
- R.G.F. Giles (Author/Creator)I.R. Green (Author/Creator)L.S. Knight (Author/Creator)V.R. Lee Son (Author/Creator)S.C. Yorkea (Author/Creator)
- Publication Details
- Journal of the Chemical Society, Perkin Transactions 1, (7), pp.865-873
- Publisher
- Royal Society of Chemistry
- Identifiers
- 991005540300307891
- Copyright
- © 1994 Royal Society of Chemistry
- Murdoch Affiliation
- Murdoch University
- Language
- English
- Resource Type
- Journal article
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