2000
DOI: 10.1021/np9905214
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Alkaloids of Andrachne aspera

Abstract: Two new 2,6-disubstituted piperidine alkaloids andrachcinine (1) and andrachcinidine (5) have been isolated from Andrachne aspera along with andrachamine and andrachcine (2). The absolute configurations of 1, 2, and 5 were established. (+)-Allosedridine and the new alkaloids (-)-8-epi-8-ethylnorlobelol I (4) and (-)-8-epihalosaline (7) were also identified as constituents of A. aspera. Structures were determined by MS and NMR techniques and by chemical conversions.

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Cited by 33 publications
(14 citation statements)
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“…The same procedure from rac‐ 21 (12.9 mg, 0.0357 mmol) gave andrachcinidine ( 6 ; 8.1 mg, 0.0356 mmol, 99 %). [ α ] D =−20.8 ( c 0.625 in CHCl 3 ) {lit 5c. [ α ] D =−20.0 (c 1.7 in CHCl 3 )}; 1 H NMR (300 MHz, CDCl 3 ): δ =3.85–3.75 (m, 1 H), 2.98 (dtd, J =11.3, 6.3, 2.5 Hz, 1 H), 2.75 (tt, J =10.7, 2.5 Hz, 1 H), 2.52 (dd, J AB =16.4, 6.3 Hz, 1 H), 2.43 (dd, J AB =16.4, 5.7 Hz, 1 H), 2.12 (s, 3 H), 1.87–1.77 (m, 1 H), 1.71–1.12 (m, 10 H), 1.10–0.99 (m, 1 H), 0.89 ppm (t, J =7.2 Hz, 3 H); 13 C NMR (75 MHz, CDCl 3 ): δ =207.5, 72.7, 58.4, 53.2, 50.5, 43.1, 40.5, 33.5, 32.5, 30.8, 24.7, 18.8, 14.3 ppm; IR (NaCl): $\tilde \nu $ =3302, 2929, 1712, 1456, 1360, 1109 cm −1 ; HRMS (ESI): m / z calcd for C 13 H 26 NO 2 : 228.1958 [ M +H] + ; found: 228.1958.…”
Section: Methodsmentioning
confidence: 99%
“…The same procedure from rac‐ 21 (12.9 mg, 0.0357 mmol) gave andrachcinidine ( 6 ; 8.1 mg, 0.0356 mmol, 99 %). [ α ] D =−20.8 ( c 0.625 in CHCl 3 ) {lit 5c. [ α ] D =−20.0 (c 1.7 in CHCl 3 )}; 1 H NMR (300 MHz, CDCl 3 ): δ =3.85–3.75 (m, 1 H), 2.98 (dtd, J =11.3, 6.3, 2.5 Hz, 1 H), 2.75 (tt, J =10.7, 2.5 Hz, 1 H), 2.52 (dd, J AB =16.4, 6.3 Hz, 1 H), 2.43 (dd, J AB =16.4, 5.7 Hz, 1 H), 2.12 (s, 3 H), 1.87–1.77 (m, 1 H), 1.71–1.12 (m, 10 H), 1.10–0.99 (m, 1 H), 0.89 ppm (t, J =7.2 Hz, 3 H); 13 C NMR (75 MHz, CDCl 3 ): δ =207.5, 72.7, 58.4, 53.2, 50.5, 43.1, 40.5, 33.5, 32.5, 30.8, 24.7, 18.8, 14.3 ppm; IR (NaCl): $\tilde \nu $ =3302, 2929, 1712, 1456, 1360, 1109 cm −1 ; HRMS (ESI): m / z calcd for C 13 H 26 NO 2 : 228.1958 [ M +H] + ; found: 228.1958.…”
Section: Methodsmentioning
confidence: 99%
“…[3] Gold-catalyzed hydration reactions were also employed in the syntheses of Pterosin B and C [4] as well as for the rapid construction of (+)-Andrachcidine. [5] By contrast the hydration of internal alkynes has not found application, probably due to the difficulty to control the regioselectivity of the transformation. [6]…”
Section: Hydration Of Alkynesmentioning
confidence: 99%
“…1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 A key step involving two gold-catalyzed hydrofunctionalisations was used in the total synthesis of the piperidine alkaloid (+)-Andrachcinidine, a chemical defence agent from the beetle Andrachne aspera. [53] Alkyne 34 was reacted with 5 mol % PhP 3 PAuCl/AgSbF 6 and H 2 O as external nucleophile to form the methyl ketone E, which eliminates MeOH. The a,b-unsaturated carbonyl compound F then undergoes subsequent 6-exo-dig hydroamination to furnish compound 35 in 90 %.…”
Section: Hydroaminationmentioning
confidence: 99%
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