Lobelia inflate

Lobeline (3), extracted from Lobelia inflate, interacts with the nicotinic receptor and could also be exploited to influence cholinergic function in AD. Other alkaloids such as sophoramine (4) and cytisine (5), found in members of the Leguminosae, also have nicotinic agonistic properties. ... 

Erangois-Xavier F, Jacques L. (2004) History, chemistry and biology of alkaloids from lobelia inflate. Tetrahedron 60 10127-10153. 

Allosedamine 157 is a relatively simple piperidine alkaloid which was isolated more than 60 years ago by Wieland and co-workers from Lobelia inflate. It has good activity against respiratory disorders such as asthma, bronchitis, and pneumonia. The key step of the current synthesis (Scheme 29) is an RCM of enone ester 155 which closes the... 

A comprehensive review article on the synthesis of piperidines by Buffat was published in 2004. The review covers many different methodologies applicable to simple piperidines and complex natural products. Pertinent literature through early 2003 is included <04T1701>. A review on the history, chemistry, and biology of the alkaloids from Lobelia inflate by Felpin and Lebreton includes useful information on the synthesis of piperidine alkaloids, with an emphasis on asymmetric methods <04T10127>. 

Lobelia. Indian tobacco wild tobacco emetic herb asthma wsed bladder pod vomit wort. Dried leaves and tops of Lobelia inflate L., Lobetiaeeae. (The seeds are also used.) Habit. Canada, U.S. ConstiL Leaves and lops chiefly lobeline, also lobelidine, lobelanine, lobelamdine. and other alkaloids. Seeds lobeline, fixed oil. 

Allosedamine (113) and (+)-sedamine (119), two piperidine alkaloids isolated from Lobelia inflate, have been used for the treatment of respiratory disorders such as asthma, bronchitis, and pneumonia. While several racemic syntheses have been reported, there are much less asymmetric ones. An enantioselective route to (—)-aUosedamine (113) was developed by Raghaven et al, which commenced with addition of lithium compound 110 to the imine 109 providing the separable aUyUc amine 111 as a 3 1 mixture of diastereoisomers (Scheme 2.27) [45, 46). Six... 

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