Tropane alkaloid ferruginine

A divergent synthesis of tropane alkaloid ferruginine was reported by Node and coworkers [59]. The P-ketoester intermediate was prepared by a novel PLE-catalyzed asymmetric dealkoxycarbonylation (hydrolysis followed by a decarboxylation) of a symmetric tropinone-type diester (Figure 6.12). Dimethyl sulfoxide was added to the phosphate buffer pH 8 (1 9) to reduce the activity of PLE and prevent over-deal-koxycarbonylation leading to tropinone. 

Numerous other alkaloids from natural origin are known ligands at nAChRs, such as the tropane alkaloid ferruginine (and several synthetic derivatives) [146,148,149], although there are limited data on their therapeutic potential in neurodegenerative diseases. Other alkaloids include the quinolizidine alkaloid C54isine (36) (occurs in... 

Recently, Ham and co-workers exploited the intramolecular aminocarbonylation in the synthesis of the tropane alkaloids rac-ferruginineand rac-anatoxin (Scheme 30). In the synthesis of rac-ferruginine the precursor for the aminocarbonylation is easily prepared in three steps from 4-cycIoheptenone. 

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