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An investigation into steric factors in the stereoselective formation of naphthopyrans from 4-naphthyldioxolanes

Green, I.R., Giles, R.G.F. and Gruchlik, Y. (1997) An investigation into steric factors in the stereoselective formation of naphthopyrans from 4-naphthyldioxolanes. South African Journal of Chemistry, 50 (2). pp. 75-81.

Abstract

The titanium tetrachloride-induced isomerisation of rel-(2R,4R,5S )- and re/-(2S,4R,5fl)-2,5-dimethyl-4-{8- bromo-4,5,7-trimethoxy-2-naphthyl) dioxolanes 16, having the C-4 oxygen protected by a methyl instead of the previously employed isopropyl group, afforded the desired linear re/-(1fl, 3fl,4fl)-6-bromo-3,4- dihydro-4-hydroxy-7,9,10-tnmethoxy -1 ,3-dimethyM H-naphtho[2,3-c] pyran 20, identified as its acetate 21, as well as the corresponding angular analogue, re/-( 1 fl,3R,4fl)-3,4-dihydro-4-hydroxy-6,7,9-trimethoxy- 1 ,3-dimethylnaphtho [1 ,2-c] pyran 22 also identified as its acetate 23…

Publication Type: Journal Article
Murdoch Affiliation: School of Mathematical and Physical Sciences
Publisher: South African Bureau for Scientific Publications
Publishers Website: http://journals.co.za/docserver/fulltext/chem/50/2...
URI: http://researchrepository.murdoch.edu.au/id/eprint/35542
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