Pyrrolidine, Pyridine and Piperidine Alkaloids

The ant venom alkaloids occurring in the genera Solenopsis and Monomorium have been reviewed briefly. The venoms of iMy latinode and M subopacum contain an array of 2,5-dialkylpyrro-lidines (1), and the pyrrolines (2) are also present. All were identified by gas-chromatographic separation followed by mass spectrometry.  

The pyrrolidine N-amide (3) has been isolated from the bark of the West African tree Hexalobus crisplflorus. Its structure was 

The roots of certain Achillea spp. contain several new amides, two of which are the pyrrolidides, (6) and (7) respectively, of 

3-dehydrolycaonic acid and lycaonic acid, Another amide from A. tomentosa L. is the pyrrolideide (8), with a centrally placed triple bond, all structures being deduced from spectral studies 4,5-Dihydro-okolasine (9) occurs in Piper guineense it has been synthesised by a Wittig-Horner reaction between 3-(2-methoxy-4, 

1 Saetetiwn Alkaloids.-A review of these alkaloids has appeared. A new alkaloid has been isolated from Crinum oliganthum. On spectral 

Two new monographs on alkaloid chemistry have appeared both contain sections on pyrrolidine, piperidine, and pyridine alkaloids.1,2 

Species of marine sponge of the genus Laxosuberites contain several pyrrole-2-aldehydes with a long side-chain at position 5. Their structures (1), (2), and (3) have been settled by spectral study and by chemical degradation. One, (3), proved to be a cyanhydrin of unusual stability.3 

Certain 2,5-dialkyl-pyrrolidines, which are trail pheromones of the pharaoh ant (Monomorium pharaonis L.), have been synthesized by application of the Hofmann-Loffler reaction to 5-aminotridecane and 7-aminopentadecane. The same type of compound results from Seebach alkylation of TV-nitrosopyrrolidines.4 

Cordell, Introduction to Alkaloids , Wiley-Interscience, Somerset, New Jersey, 1981. 

A new monograph on alkaloid chemistry has been published parts of it are devoted to pyrrolidine, piperidine, and pyridine alkaloids.1 A review on the synthesis of alkaloids via nitrones has appeared,2 and another on the photochemistry of alkaloids, which includes a section on alkaloids of this group.3 

Dalton, The Alkaloids. The Fundamental Chemistry , Marcel Dekker, New York and Basel, 1979, Parts 2, 3, and 4. 

The principal component of the secretion of the poison gland of the European thief ant (Solenopsis fugax) is rrarcs-2-n-butyl-5-n-heptylpyrrolidine, identified by mass spectrometry and synthesis.5 The reductive amination of 1,4-diketones with sodium cyanoborohydride and ammonium acetate has yielded various 2,5-dialkyl-pyrrolidines that occur in the poison glands of ants of Monomorium spp.6 

The leaves of Aglaria roxburghiana contain roxburghilin, a bis-amide that has been shown to be jV-cinnamoyl-2-(2-methylbutanoylamino)pyrrolidine (9) 

Croomine is a major alkaloid of the roots and rhizomes of Croomia heterosepala. Its structure (10) has been settled by its chemical reactions and spectroscopic properties, and confirmed by X-ray diffraction analysis of its methiodide. On mild oxidation (dehydrogenation) with silver oxide, the alkaloid affords the corresponding pyrrole.8 

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Chapter 2 Pyrrolidine, Piperidine, and Pyridine Alkaloids By A. R. Pinder... 

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