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Pellitorine

Diene carboxylates can be prepared by the reaction of alkenyl halides with acrylates[34]. For example, pellitorine (30) is prepared by the reaction of I-heptenyl iodide (29) with an acrylate[35]. Enol triflates are reactive pseudo-halides derived from carbonyl compounds, and are utilized extensively for novel transformations. The 3,5-dien-3-ol triflate 31 derived from a 4,5-unsaturated 3-keto steroid is converted into the triene 32 by the reaction of methyl acrylate[36]. [Pg.132]

When allylic compounds are treated with Pd(0) catalyst in the absence of any nucleophile, 1,4-elimination is a sole reaction path, as shown by 492, and conjugated dienes are formed as a mixture of E and Z isomers[329]. From terminal allylic compounds, terminal conjugated dienes are formed. The reaction has been applied to the syntheses of a pheromone, 12-acetoxy-1,3-dode-cadiene (493)[330], ambergris fragrance[331], and aklavinone[332]. Selective elimination of the acetate of the cyanohydrin 494 derived from 2-nonenal is a key reaction for the formation of the 1,3-diene unit in pellitorine (495)[333], Facile aromatization occurs by bis-elimination of the l,4-diacetoxy-2-cyclohex-ene 496[334],... [Pg.356]

The telomer 137, obtained by the reaction of butadiene with malonate, is a suitable compound for the syntheses of naturally occurring dodecanoic acid derivatives, such as queen substance (I38)[l 7], one of the royal jelly acids (139)[I18], and pellitorine fl40)[ll9]. [Pg.444]

Pelletierine and associated bases, pharmacological action, 62, 108 isoPelletierine, 55, 57, 58 pserwfoPelletierine, 55, 58 constitution, 59 synthesis, 61 Pellitorine, 2... [Pg.798]

Butylnona-1 5-diene- 1-carboxyamides and the Strukture of Pellitorine. J. Chem. Soc. [London] 1952, 4338. [Pg.268]

Another useful compound is the 1 2 telomer of malonate and butadiene, 137. The first example is the synthesis of pellitorine (138), a naturally occurring pesticide (126). The terminal double bond was hydrogenated selectively with RuCl2(PPh3)3 as a catalyst. Partial hydrolysis afforded the monoester, which was treated with PhSeSePh to displace one of the carboxyl group with phenylselenyl group. Oxidative removal of the phenylselenyl group afforded 2,4-decadienoate (139), which is converted to pellitorine (138) ... [Pg.187]

Ene reactions of Pummerer-type reaction intermediates have been used as key steps in the synthesis of both pellitorine and trichonine. ... [Pg.543]

Five isobutylamides were isolated as insect growth inhibitors and toxicants from Fagara macrophylla and identified from their spectroscopic and chemical data. Synthesis and bioassay of the five natural products plus four analogs showed pellitorine to be the most active against a variety of insects, but not against a species of snail. [Pg.163]

LDoQ-value, the lethal dose for 90 death, for pellitorine against P. gossypiella is 25 ppm. [Pg.165]

Thus, the most potent of the natural isobutylamides was pellitorine (4), while the most potent of the synthetic isobutylamides was the cis isomer il) of fagaramide (J ). [Pg.167]

Through a comparison of the activities of the nine natural and synthetic compounds in Table I, certain functionalities appeared to be important in the efficacy of the isobutylamides to inhibit the growth of the lepidopterous larvae. These functionalities included the chain length, presence of the methylenedioxy moiety, the number of the side chain double bonds, and the stereochemistry of the side chain. Combinations of these functionalities would likely enhance the activity. For instance, Miyakado et al.H found that addition of the methylenedioxy moiety to pellitorine (4) increased its toxicity when topically applied to adults of the beetle, Callosobruchus chinensis. [Pg.167]

Pellitorine (4) has long been known for its toxicity when topically applied to adults of the beetle, Tenebrio molitor We found that 10 pg doses of topically applied pellitorine caused a paralytic action on adults of the confused flour beetle, Tribolium confusum (unpublished data). However, all of the affected beetles recovered within 24 hrs posttreatment. Similar topical applications of up to 20 pg/beetle of fagaramide (2.), piperlongumine ( ), and N-isobutyl-2E,4E-octadienamide ( ) proved ineffective. [Pg.167]

The lethal activity of the isobutylamides on C. pipiens is shown in Table II. The amides were dissolved in 0.1% acetone in distilled water to give concentrations of 1-20 ppm. Third-instar C. pipiens were transferred (5 larvae/10 ml test solution) into 1 oz. plastic cups using a 1 x 1-inch circle of ordinary window screen. Each treatment was replicated 4 times and the minimum concentration of each compound which caused 100% mortality (LDioo) within 48 h at 25 C and 16L/8D photoperiod was determined. In a result similar to that found with the artificial diet bioassay with lepidopterous larvae, pellitorine proved to be the most toxic of the assayed amides (LDjqq = 5 ppm). [Pg.167]

The lethal activity of the isobutylamides on B. glabratus is shown in Table III. Molluscicidal activity was monitored as described previously.Briefly, snails of uniform sizes (average diameter of the shell 9 mm) were placed 2 snails/ concentration into deionized water solutions containing known concentrations of the isobutylamides. Unlike the relative activities of the isobutylamides on the tested insect species, fagaramide (1 ) and N-isobutyl-2E,4E -octadienamide ( ) were more potent molluscicides than were pellitorine (4) or piperlongumine (2). [Pg.170]

While the F. macrophylla isobutylamides, especially pellitorine, are active against several species of pest organisms of medical and agricultural importance, their activity must be enhanced before they can be used on a commercial basis. Hopefully, the results of the present work will direct future studies leading to synthetic isobutylamides of sufficient activity to warrant their practical use in insect and snail control. [Pg.170]

In 2004, Ley et al. [45] showed a stereoselective enzymatic synthesis of cis-pellitorine [N-isobutyldeca-(2 ,4Z)-dienamide], a taste-active alkamide naturally occurring in tarragon. The reactants were ethyl ( ,Z)-2,4-decadienoate— the pear ester described before—and isobutyl amine. The reaction is catalysed by lipase type B from Candida antarctica (commercially available), which shows a remarkable selectivity towards the 2 ,4Z ester. The yield was about 80%. [Pg.493]

The two sulfur-containing amides entadamides A (93) and B (94) have been isolated from the seeds and entadimides A and C (95) from the leaves of Entada phaseoloides Merr. (valid name Entada rheedii Spreng.) (Legu-minosae) (99-101). The known isobutylamide alkaloid pellitorine (N-isobutyl-2 ,4 -decadienamide) is found in the aerial parts of Piper ri-besoides Wall. (102). Pellitorine has also been isolated from the fruits of P. [Pg.33]

Semple, J. E. A concise synthesis of pellitorine. Organic Preparations and Procedures International 1995, 27, 582-586. [Pg.208]

Returning to the question in the title of this section, capsaicin does not fall into any of the three classic types of nitrogen-bearing plant natural products, being neither a true alkaloid, a protoalkaloid, or a pseudoalkaloid. Capsaicin is oflimited distribution in Nature and shows pharmacological activity, but is non-basic, structurally unsophisticated, and not directly derived from an amino acidic precursor. On the other hand, the lack of attributes such as basicity, complexity, and an amino acidic pedigree can also be found in compounds commonly perceived as alkaloids. Thus, colchicine is neutral, ephedrine is structurally unsophisticated, and the nitrogen atom of the potato alkaloid solanine is not derived from an amino acid, but rather incorporated into as non-amino acidic framework by a transamination reaction. For the sake of clarity and consistency, it seems therefore convenient to adopt the modern definition of alkaloids, and consider capsaicin, as well as alkylamides such as piperine (18) and pellitorine (19), as such. [Pg.77]


See other pages where Pellitorine is mentioned: [Pg.2]    [Pg.193]    [Pg.194]    [Pg.194]    [Pg.195]    [Pg.269]    [Pg.164]    [Pg.164]    [Pg.165]    [Pg.168]    [Pg.169]    [Pg.170]    [Pg.171]    [Pg.471]    [Pg.385]    [Pg.351]    [Pg.20]    [Pg.354]    [Pg.464]    [Pg.27]    [Pg.35]   
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See also in sourсe #XX -- [ Pg.171 ]




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