Issue 7, 1994
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

Robin G. F. Giles,   Ivan R. Green,   Lorraine S. Knight,   Vanessa R. Lee Son  and  Selwyn C. Yorkea  

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.

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Article information

DOI
https://doi.org/10.1039/P19940000865
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1994, 865-873

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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

R. G. F. Giles, I. R. Green, L. S. Knight, V. R. Lee Son and S. C. Yorkea, J. Chem. Soc., Perkin Trans. 1, 1994, 865 DOI: 10.1039/P19940000865

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