The total synthesis of natural (+)-varitriol (1) was accomplished by starting from dimethyl L-tartrate. The key features were a substrate selective and diastereoselective PdII-catalysed bicyclisation of unsaturated protected triol 9 followed by regioselective ring-opening of bicyclic skeleton 10. The absolute configuration of the target was confirmed by single-crystal X-ray analysis for the first time.
Palik, Miroslav,Karlubikova, OL'Ga,Lasikova, Angelika,Kozisek, Jozef,Gracza, Tibor
experimental part
p. 709 - 715
(2009/07/19)
THE SELECTIVE BENZYLIC BROMINATION OF o-XYLENES. A USEFUL SYNTHESIS OF PHTHALIDES
The free radical bromination of aryl methyl groups can be controlled by the strategic positioning of a remote stereo-electronic blocking group on the aryl ring.This tactic leads to the efficient synthesis of selectively benzylically brominated molecules which are useful synthetic intermediates.This methodology has been applied to the synthesis of some phthalides.
Box, Vernon, G. S.,Yiannikouros, George P.
p. 1261 - 1270
(2007/10/02)
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