R. Giles, Joshua D. McManus
Nov 18, 2009
Citations
0
Influential Citations
7
Citations
Journal
Tetrahedron Letters
Abstract
The rearrangement of (2′S,4′R,5′S)-2-(2′,5′-dimethyl-1′,3′-dioxolan-4′-yl)-4,5,7-trimethoxynaphthalen-1-yl 4″-methylbenzenesulfonate with titanium(IV) chloride affords (1R,3S,4R)-10-chloro-6,7,9-trimethoxy-1,3-dimethyl-3,4-dihydro-4-hydroxynaphtho[1,2-c]pyran in good yield. This transformation is characterized by two unusual aromatic substitution reactions in that, in one, tosyloxy is lost and, in the other, aromatic chlorination occurs with titanium(IV) chloride as the source of chlorine.