Pyridine-piperidine alkaloids

These alkaloids have their nitrogen atoms in typical six-membered rings, which in the case of pyridine is a benzene ring. The precursors are generally ornithine and nicotinic acid although lobeline has a unique biosynthesis (see below). 

Coniine, a-propylpiperidine, is found in spotted hemlock— Conium maculatum (Apiaceae). It is a piperidine structure with a short ahphatic side chain, and is a volatile oily compound. Coniine is very toxic and causes death by paralysis. 

Nicotine, l-methyl-2 (3-pyridyl) pyrrolidine, is found in tobacco derived from Nicotiana tabacum and other plants of the Solanaceae, including the Australian pituri (Duboisia hopwoodii), whose properties were exploited by the indigenous Australians of the central desert 

Atropa belladonna Erythroxylon coca Datura mete  

Chelidonium majus Pneumus boldo Cephaelis ipecacuanha 

---

Contains about 0.48% pyridine (piperidine) alkaloids composed mainly of lobeline, with lesser amounts of lobelanine and lobelanidine. Other alkaloids present include norlobelanine (isolobelanine), lelobanidine, norlelobanidine, norlobelanidine, lobinine, isolobinine, lobina-nidine, isolobinanidine, 8-methyl-10-ethyllo-belidiol, and 8-methyl-10-phenyllobelidiol, among others. ... 

Fodor, G.B. and Colasanti, B. (1985). The pyridine and piperidine alkaloids chemistry and pharmacology, in Pelletier S., Ed., Alkaloids chemical and biological perspectives, Vol. 3, John Wiley and Sons, New York, pp. 3-91. 

O Hagan, D. 2000. Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids. Nature Product Reports, 17 435 46. 

The term chromone alkaloid is used to describe a structure consisting of a pyridine, piperidine, or pyrrolidine ring linked to the A ring of chromone (1). In... 

Schneider MJ (1996) Pyridine and piperidine alkaloids an update. Alkaloids, Chemical and Biological Perspectives (ed Pelletier SW) Vol 10. Elsevier, Amsterdam, pp 155-299. 

Chiral Lewis acids have been employed by Yamamoto et al. [197 -199] in order to carry out enantioselective aza Diels-Alder reactions starting from achiral substrates however, these transformations required stoichiometric amounts of the chiral mediator 3-16 which was generated in situ from (fl)-binaphthol and triphenylborate. The best results were obtained with the pyridine derivative 3-14 which afforded the desired cycloadduct 3-15 in high optical purity (Fig. 3-5). Using chiral imines, the authors found a high level of double asymmetric induction, and this methodology could be applied to the enantioselective total synthesis of two piperidine alkaloids. 

Nicotine and related pyridine alkaloids (A) Ammodendrine (A) anabasine (A) arborine (AA) boldine and other aporphine alkaloids (AA) berberine and related protoberberine alkaloids C-toxiferine (AA) coniine and related piperidine alkaloids (A) cytisine, lupanine, and other quinolizidine alkaloids (A) tubocurarine (AA) codeine (A) erysodine and related Erythrina alkaloids (AA) histrionicotoxin (AA) lobeline (A) methyllycaconitine (AA) pseudopelletierine (A)... 

Klingsberg, E. and Newkome, G.R., Eds., Pyridine and Its Derivatives, Interscience, New York, 1960 Schoefield, K., Heteroaromatic Nitrogen Compounds Pyrroles and Pyridines, Butterworths, London, 1967 Hurst, D.T., An Introduction to the Chemistry and Biochemistry and Pyrimidines, Purines, and Ptreridines, J. Wiley, Chichester, UK, 1980 Plunkett, A.O., Pyrrole, pyrrolidine, pyridine, piperidine, and azepine alkaloids, Nat. Prod. Rep. 11, 581-590, 1994 Kaiser, J.P., Feng, Y., and Bollag, J.M., Microbial metabolism of pyridine, quinoline, acridine, and their derivatives under aerobic and anaerobic conditions, Microbiol. Rev. 60, 483-498, 1996. 

II.1. PYRROLIZIDINE, PYRIDINE, PIPERIDINE AND QUINOLIZIDINE ALKALOIDS Chapter 4... 

The intent of this chapter is to provide an update of pyridine and piperidine alkaloid literature since this topic was last covered in Volume 3 of this series [1], The approximate time period covered by this review is 1984-1994. Due to the wealth of information available, this review had to be somewhat selective. For example, with the exception of a few selected pyridine monoterpenes, alkaloids containing a pyridine or piperidine ring fused to another ring system were excluded. The focus of this review is placed on describing new compounds isolated, biosynthesis, and biological properties. Synthesis has not been emphasized in most cases reference is made to only the most recent syntheses. 

---