Nauclefine et naucletine deux nouveaux alcaloides de type indoloquinolizidine isoles du Nauclea latifolia

Hotellier, F; Delaveau, Pierre; Pousset, Jean-Louis

doi:10.1016/s0031-9422(00)98638-2

Cited by 55 publications

(41 citation statements)

References 4 publications

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“…This oxidation iiivolves traiisforming the viiiyl group to an epoxidc equivalent, probably after the initial condensation forming viilcoside (1 l), and reaction of this unit with tlie a n~i n o function can lead to the hydroxylated seven-membered ring. (It seems likely that the alkaloids of N. Ic~t[folic~ (12) arise by a sequence correspoiiding t o that outlined below, but without formation of this seven~ilembered ring; instead, lactaniization occurs at a subsequent stage.) A fi~rtlier oxidation would form cadambine, 23, and obvious ~nodifications would lead to isodihydrocadaiiibine (10) and rubeniiie, 13, which have been isolated from related species.…”

mentioning

confidence: 84%

“…Removal of the solvent afforded a yellow oil which was purified by preparative tlc with rn-rn-a elution. The oxazolidine 18 ( R = Ph) was obtained as an oil (166 rng, 0.55 rnrnol): ir 2.90, 3.04; uv 225 (20 600), 250 (6200), 274 (3800), 282 (3800), 291 (3300), 360 (11 400); in MeOH-HCI 214 (16 600), 250 (10 400), 362 (23 500); in MeOH-KOH 229 (24 900), 275 (8300), 282 (8300), 291 (7100); nrnr (areas based on 50:50 mixture of two CzoHzoN20 isomers) 1.36 (s, l H , removed by D20), 1.53 (s, l H , removed by DzO), 2.4-3.0 (complex, 18H), 4.66 (4 peaks, separations 6, 4, 6 Hz, lH), 5.12 (4 peaks, separations 6, 1, 6 Hz, lH), 6.4-7.6 (complex, 12H), 8.21 (s, 3H, removed by D20), 8.26 (s, 3H, removed by DzO); rns 305 (5), 304 (14), 290 (20), 289 (loo), 200 (5), 199 (13), 198 (57), 197 (12), 185 (6), 184 (6), 183 (12), 182 (6), 172 (15), 171 (7), 170 (12).…”

Section: Model Cottlpound 18 ( R = Pi/)mentioning

confidence: 99%

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Constituents of Naucleadiderrichii. Part VII. Synthesis of nauclederine, naucleonine, and naucleonidine; spectroscopic evidence for the structures of 3α-dihydrocadambine and two other constituents

McLean¹,

Dmitrienko²,

Szakolcai³

1976

Can. J. Chem.

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STEWART MCLEAN, GARY I. DMITRIENKO, and AKOS SZAKOLCAI. Can. J. Chem. 54, 1262Chem. 54, (1976.Evidence is advanced concerning the structures of six N. rlirlrrriclrii alkaloids, based on synthetic and spectroscopic studies. The synthesis of nauclederine, 2, provides support for the structural assignment made earlier. Synthesis has shown that the structures previously assigned to the alkaloids designated ND-305B and ND-363C are incorrect; this, however, has led to revised structures (19 and 20) for these alkaloids, now named naucleonine and naucleonidine, respectively, and these have been established by synthesis. Based on this study and an examination of data obtained previously, a tentative proposal is made for the structure 21 of another constituent of the plant, designated ND-363B. Spectroscopic studies have allowed a structure 22 to be advanced for the glycosidic alkaloid, which was shown to be identical with the alkaloid 3a-dihydrocadambine obtained by Brown and Fraser. Based on this study and a reexamination of data reported previously, structure 25 is tentatively proposed for another constituent of the plant, designated ND-370.STEWART MCLEAN, GARY I. DMITRIENKO et AKOS SZAKOLCAI. Can. J. Chem. 54,1262Chem. 54, (1976. On prkente des donnCes, basCes sur des Ctudes de synthkse et de spectroscopic, concernant la structure de six alcalo'ides N. dirlrrt-icllii. La synthkse de la nauclederine, 2, fournit une preuve supplkmentaire pour I'attribution de structure proposCe anttrieurement. On a dCmontrC, par synthkse, que les structures proposees anterieurement pour les alcalo'ides ND-305 B et ND-363C ne sont pas correctes. Nos Ctudes ont toutefois permis d'attribuer les structures revisies (19 et 20) B ces alcaloi'des qui sont maintenant nommes respectivement naucleonine et naucleonidine; ces structures ont maintenant ett etablies par synthkse. En se basant sur I'Ctude prisente et en reexaminant les donnees obtenues anterieurement, une structure non-definitive 21 est proposie pour le constituant ND-363B de la plante. Des etudes spectroscopiques ont permis de proposer la structure 22 pour I'alcalo'ide glycosidique; on a montrC que cet alcalo'ide est identique avec I'alcalo'ide 3cr dihydrocadambine obtenu par Brown et Fraser. En se basant sur I'Ctude act~elle et B I'aide d'un reexamen des donnCes obtenues anterieurement, oq propose, d'une f a~o n nondefinitive, la structure 25 pour le constituant ND-370 de la plante.[Traduit par le journal]We have described the isolation of constituents of Nauclea diderrichii which, for convenience, we have placed in four categories (1). The structures of all of the members of the first two groups, the simple P-carbolines and the sinlple pyridines were established with confidence (la). In the third group, the indole-pyridine alkaloids, only naucledine, 1, was assigned a structure unequivocally, but provisional structures were advanced for other members of the group with varying degrees of confidence (lb). Structural assignments to the members of the fourth group, miscellaneous sub...

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mentioning

confidence: 84%

Section: Model Cottlpound 18 ( R = Pi/)mentioning

confidence: 99%

Constituents of Naucleadiderrichii. Part VII. Synthesis of nauclederine, naucleonine, and naucleonidine; spectroscopic evidence for the structures of 3α-dihydrocadambine and two other constituents

McLean¹,

Dmitrienko²,

Szakolcai³

1976

Can. J. Chem.

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“…[3] Nauclefine (1), [4] angustine (2), [5] ate capable of an easy conversion (1Ϫ2 steps) into the finaucletine (4), [4] angustoline (5), [5,6] 19-O-methylangusto-nal products. line (6), [7] and naulafine (7) [8] may be listed among the most representative alkaloids of this structural type.…”

Section: Introductionmentioning

confidence: 99%

A Unified Synthetic Strategy for the Indolopyridine Alkaloid Group

Lavilla¹,

Gullón

Bosch

1999

Eur. J. Org. Chem.

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“…A number of monoterpene indole alkaloids such as nauclefine 1) and naulafine 2) have been isolated from plants of Nauclea species (Rubiaceae). Recently, several monoterpene indole alkaloids have been isolated from Nauclea orientalis which have interesting biological activity.…”

mentioning

confidence: 99%

“…3,4) In our search for structurally unique constituents from higher plants, five new monoterpene indole alkaloids, naucleamides A-E (1-5), have been isolated from the bark and wood of Nauclea latifolia. 1,2) Nauleamide E (5) is a monoterpene indole alkaloid possessing a pentacyclic ring system with an amino acetal bridge. In this paper we describe the isolation and structural elucidation of 1-5.…”

mentioning

confidence: 99%