Facile protection of phenols and hydroxypyridines: key components of natural products--a new pathway to orellanine.
The (1,3,6-trioxa-heptyl) aromatic compounds are easily prepared from various phenols and hydroxypyridines. Protection by 2-methoxyethoxymethyl chloride (MEM-Cl) was achieved by phase transfer catalysis with Aliquat 336, subsequent removal of the protecting group was completed with Amberlyst 15. The 2-bromo-3-hydroxy-pyridine 3o constitutes the appropriate starting material for the synthesis of orellanine, the most potent nephrotoxin found in some Cortinarius mushrooms species.
Michelot
Didier
D
Laboratoire de Chimie des Substances Naturelles, ESA 8041 CNRS, Muséum National d'Histoire Naturelle, 63, rue de Buffon, F-75005 Paris, France. michelot@mnhn.fr
Meyer
Michele
M
D015082:2,2'-Dipyridyl / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D000363:Agaricales / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry
D010636:Phenols; D011725:Pyridines; D000644:Quaternary Ammonium Compounds; C014047:hydroxypyridines; C030076:orellanine; C037759:trioctylmethylammonium; D015082:2,2'-Dipyridyl