Extractives from Guttiferae. Part 33. Synthesis of the ozonolysis product from dimethylmangostin, 1-hydroxy-3,6,7-trimethoxy-2,8-bis-(2-oxoethyl)xanthone; some 13C nuclear magnetic resonance spectra of xanthones
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 19,p. 2158-2162
- https://doi.org/10.1039/p19770002158
Abstract
The synthesis of the dialdehyde 1-hydroxy-3,6,7-trimethoxy-2,8-bis-(2-oxoethyl)xanthone, first obtained from ozonolysis of dimethylmangostin, is described. Xanthone formation by cyclisation of a benzophenone intermediate is followed by selective demethylations, allylation, and Claisen rearrangement. Oxidative cleavage of the allyl side chains in 2,8-diallyl-1,3,6,7-tetramethoxyxanthone, followed by demethylation with boron trichloride, gave the required dialdehyde (5). Some 13C n.m.r. spectra of xanthones are discussed.This publication has 1 reference indexed in Scilit: