Microbial C-hydroxylation and β-4-O-methylglucosidation of methyl-benzamide 7-azanorbornane ethers with Beauveria bassiana
2002; Elsevier BV; Volume: 21; Issue: 3 Linguagem: Inglês
10.1016/s1381-1177(02)00081-4
ISSN1873-3158
AutoresHoracio F. Olivo, Tonya L. Peeples, Marı́a-Yolanda Rı́os, Francisco Velázquez, Jin Woo Kim, Someet Narang,
Tópico(s)Chemical synthesis and alkaloids
ResumoN-Substituted 7-azanorbornanes were prepared by acylation of easily accessible 7-azanorbornane hydrochloride. Derivatives possessing an electron-withdrawing docking/protecting group and bearing an aryl methylether were subjected to biotransformation with the fungus Beauveria bassiana ATCC 7159. O-Demethylation and β-4-O-methylglucosidation reactions were observed for the major metabolite in this biotransformation (isolation yields: 6, 30%; 11a, 44%; 11b, 47%; 11c, 14%). C-Hydroxylation on an unfunctionalized carbon was also observed in most of the cases.
Referência(s)