Ancistrocladinium A and B, the first N,C-coupled naphthyldihydroisoquinoline alkaloids, from a Congolese Ancistrocladus species

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Ancistrocladinium A and B, the first N,C-coupled naphthyldihydroisoquinoline alkaloids, from a Congolese Ancistrocladus species. / Bringmann, Gerhard; Kajahn, Inga; Reichert, Matthias; Pedersen, Sarah E.H.; Faber, Johan H.; Gulder, Tanja; Brun, Reto; Christensen, Søren B.; Ponte-Sucre, Alicia; Moll, Heidrun; Heubl, Günther; Mudogo, Virima.

In: Journal of Organic Chemistry, Vol. 71, No. 25, 08.12.2006, p. 9348-9356.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Bringmann, G, Kajahn, I, Reichert, M, Pedersen, SEH, Faber, JH, Gulder, T, Brun, R, Christensen, SB, Ponte-Sucre, A, Moll, H, Heubl, G & Mudogo, V 2006, 'Ancistrocladinium A and B, the first N,C-coupled naphthyldihydroisoquinoline alkaloids, from a Congolese Ancistrocladus species', Journal of Organic Chemistry, vol. 71, no. 25, pp. 9348-9356. https://doi.org/10.1021/jo061626w

APA

Bringmann, G., Kajahn, I., Reichert, M., Pedersen, S. E. H., Faber, J. H., Gulder, T., Brun, R., Christensen, S. B., Ponte-Sucre, A., Moll, H., Heubl, G., & Mudogo, V. (2006). Ancistrocladinium A and B, the first N,C-coupled naphthyldihydroisoquinoline alkaloids, from a Congolese Ancistrocladus species. Journal of Organic Chemistry, 71(25), 9348-9356. https://doi.org/10.1021/jo061626w

Vancouver

Bringmann G, Kajahn I, Reichert M, Pedersen SEH, Faber JH, Gulder T et al. Ancistrocladinium A and B, the first N,C-coupled naphthyldihydroisoquinoline alkaloids, from a Congolese Ancistrocladus species. Journal of Organic Chemistry. 2006 Dec 8;71(25):9348-9356. https://doi.org/10.1021/jo061626w

Author

Bringmann, Gerhard ; Kajahn, Inga ; Reichert, Matthias ; Pedersen, Sarah E.H. ; Faber, Johan H. ; Gulder, Tanja ; Brun, Reto ; Christensen, Søren B. ; Ponte-Sucre, Alicia ; Moll, Heidrun ; Heubl, Günther ; Mudogo, Virima. / Ancistrocladinium A and B, the first N,C-coupled naphthyldihydroisoquinoline alkaloids, from a Congolese Ancistrocladus species. In: Journal of Organic Chemistry. 2006 ; Vol. 71, No. 25. pp. 9348-9356.

Bibtex

@article{12fe63645df3422487994893b3317e53,
title = "Ancistrocladinium A and B, the first N,C-coupled naphthyldihydroisoquinoline alkaloids, from a Congolese Ancistrocladus species",
abstract = "(Chemical Equation Presented) The isolation and structural elucidation of three novel-type naphthylisoquinoline alkaloids, ancistrocladinium A and B (the latter along with its atropisomer), from a Congolese Ancistrocladus species collected in the habitat Yeteto is reported. Their structures, including all stereochemical features, were elucidated by spectroscopic, chemical, and chiroptical methods. Ancistrocladinium A and B are the first N,C-coupled naphthyldihydroisoquinoline alkaloids found in nature, i.e., with an iminium-aryl axis. Although ancistrocladinium A, which is N,8′-coupled, is configurationally stable at this axis, ancistrocladinum B and its rotational isomer are based on a hitherto unprecedented N,6′-coupling type, with a slow rotation about the hetero biaryl axis at room temperature; they thus occur as a 46:54 mixture of two configurationally semistable atropo-diastereomers. For the isomerization of (P)-ancistrocladinium B to its (M)-diastereomer and for the opposite direction, the Gibbs free energies of activation were determined to be ΔG‡1 = 105.8 kJ mol-1 and ΔG‡2 = 105.7 kJ mol-1, respectively. In addition, the compounds were shown to have promising antileishmanial activities.",
author = "Gerhard Bringmann and Inga Kajahn and Matthias Reichert and Pedersen, {Sarah E.H.} and Faber, {Johan H.} and Tanja Gulder and Reto Brun and Christensen, {S{\o}ren B.} and Alicia Ponte-Sucre and Heidrun Moll and G{\"u}nther Heubl and Virima Mudogo",
year = "2006",
month = dec,
day = "8",
doi = "10.1021/jo061626w",
language = "English",
volume = "71",
pages = "9348--9356",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "25",

}

RIS

TY - JOUR

T1 - Ancistrocladinium A and B, the first N,C-coupled naphthyldihydroisoquinoline alkaloids, from a Congolese Ancistrocladus species

AU - Bringmann, Gerhard

AU - Kajahn, Inga

AU - Reichert, Matthias

AU - Pedersen, Sarah E.H.

AU - Faber, Johan H.

AU - Gulder, Tanja

AU - Brun, Reto

AU - Christensen, Søren B.

AU - Ponte-Sucre, Alicia

AU - Moll, Heidrun

AU - Heubl, Günther

AU - Mudogo, Virima

PY - 2006/12/8

Y1 - 2006/12/8

N2 - (Chemical Equation Presented) The isolation and structural elucidation of three novel-type naphthylisoquinoline alkaloids, ancistrocladinium A and B (the latter along with its atropisomer), from a Congolese Ancistrocladus species collected in the habitat Yeteto is reported. Their structures, including all stereochemical features, were elucidated by spectroscopic, chemical, and chiroptical methods. Ancistrocladinium A and B are the first N,C-coupled naphthyldihydroisoquinoline alkaloids found in nature, i.e., with an iminium-aryl axis. Although ancistrocladinium A, which is N,8′-coupled, is configurationally stable at this axis, ancistrocladinum B and its rotational isomer are based on a hitherto unprecedented N,6′-coupling type, with a slow rotation about the hetero biaryl axis at room temperature; they thus occur as a 46:54 mixture of two configurationally semistable atropo-diastereomers. For the isomerization of (P)-ancistrocladinium B to its (M)-diastereomer and for the opposite direction, the Gibbs free energies of activation were determined to be ΔG‡1 = 105.8 kJ mol-1 and ΔG‡2 = 105.7 kJ mol-1, respectively. In addition, the compounds were shown to have promising antileishmanial activities.

AB - (Chemical Equation Presented) The isolation and structural elucidation of three novel-type naphthylisoquinoline alkaloids, ancistrocladinium A and B (the latter along with its atropisomer), from a Congolese Ancistrocladus species collected in the habitat Yeteto is reported. Their structures, including all stereochemical features, were elucidated by spectroscopic, chemical, and chiroptical methods. Ancistrocladinium A and B are the first N,C-coupled naphthyldihydroisoquinoline alkaloids found in nature, i.e., with an iminium-aryl axis. Although ancistrocladinium A, which is N,8′-coupled, is configurationally stable at this axis, ancistrocladinum B and its rotational isomer are based on a hitherto unprecedented N,6′-coupling type, with a slow rotation about the hetero biaryl axis at room temperature; they thus occur as a 46:54 mixture of two configurationally semistable atropo-diastereomers. For the isomerization of (P)-ancistrocladinium B to its (M)-diastereomer and for the opposite direction, the Gibbs free energies of activation were determined to be ΔG‡1 = 105.8 kJ mol-1 and ΔG‡2 = 105.7 kJ mol-1, respectively. In addition, the compounds were shown to have promising antileishmanial activities.

UR - http://www.scopus.com/inward/record.url?scp=33845514124&partnerID=8YFLogxK

U2 - 10.1021/jo061626w

DO - 10.1021/jo061626w

M3 - Journal article

C2 - 17137361

AN - SCOPUS:33845514124

VL - 71

SP - 9348

EP - 9356

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 25

ER -

ID: 232592889