Tetrahedron

, volume 61 , issue 9 , pages 2505-2511

Synthesis and structural revision of naturally occurring ayapin derivatives

Dominick Maes ¹

Stijn Vervisch ¹

Silvia Debenedetti ²

Carlos Davio ³

Sven Mangelinckx ¹

Nicola Giubellina ¹

Norbert De Kimpe ¹

Hide authors affiliations Show authors affiliations: 3 affiliations

Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University Coupure Links 653, B-9000 Ghent, Belgium |

Department of Biological Sciences, Faculty of Sciences, National University of La Plata, Calle 115 and 47, 1900 La Plata, Argentina |

Laboratory of Radioisotopes, Faculty of Pharmacy and Biochemistry, University of Buenos Aires, Junin 956, 1113 Buenos Aires, Argentina |

Publication type: Journal Article

Publication date: 2005-02-01

Elsevier

Tetrahedron

scimago Q3

wos Q2

SJR: 0.426

CiteScore: 4.1

Impact factor: 2.2

ISSN: 00404020, 14645416

DOI: 10.1016/j.tet.2004.12.061

Copy DOI

Organic Chemistry

Drug Discovery

Biochemistry

Abstract

The synthesis of three highly oxygenated naturally occurring coumarins, 8-methoxy-6,7-methylenedioxycoumarin, 5-methoxy-6,7-methylenedioxycoumarin and 5,8-dimethoxy-6,7-methylenedioxycoumarin is described for the first time, together with a new method for the preparation of ayapin (6,7-methylenedioxycoumarin). Comparison of the spectroscopic data of the synthetic tetraoxygenated coumarin 5,8-dimethoxy-6,7-methylenedioxycoumarin with literature reports resulted in the structural revision of several natural coumarins. Two coumarins, both identified as 5,8-dimethoxy-6,7-methylenedioxycoumarin must have other structures, while the structure of another coumarin, described as the isomeric 7,8-dimethoxy-5,6-methylenedioxycoumarin has to be revised to 5,8-dimethoxy-6,7-methylenedioxycoumarin.

Found

1 citation

Nasyrova Darina

🤝

23 publications, 88 citations

h-index: 5

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Crystallography

X-ray diffraction (XRD)

X-ray diffraction analysis

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GOST |

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GOST Copy

Maes D. et al. Synthesis and structural revision of naturally occurring ayapin derivatives // Tetrahedron. 2005. Vol. 61. No. 9. pp. 2505-2511.

GOST all authors (up to 50) Copy

Maes D., Vervisch S., Debenedetti S., Davio C., Mangelinckx S., Giubellina N., De Kimpe N. Synthesis and structural revision of naturally occurring ayapin derivatives // Tetrahedron. 2005. Vol. 61. No. 9. pp. 2505-2511.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1016/j.tet.2004.12.061

UR - https://doi.org/10.1016/j.tet.2004.12.061

TI - Synthesis and structural revision of naturally occurring ayapin derivatives

T2 - Tetrahedron

AU - Maes, Dominick

AU - Vervisch, Stijn

AU - Debenedetti, Silvia

AU - Davio, Carlos

AU - Mangelinckx, Sven

AU - Giubellina, Nicola

AU - De Kimpe, Norbert

PY - 2005

DA - 2005/02/01

PB - Elsevier

SP - 2505-2511

IS - 9

VL - 61

SN - 0040-4020

SN - 1464-5416

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2005_Maes,

author = {Dominick Maes and Stijn Vervisch and Silvia Debenedetti and Carlos Davio and Sven Mangelinckx and Nicola Giubellina and Norbert De Kimpe},

title = {Synthesis and structural revision of naturally occurring ayapin derivatives},

journal = {Tetrahedron},

year = {2005},

volume = {61},

publisher = {Elsevier},

month = {feb},

url = {https://doi.org/10.1016/j.tet.2004.12.061},

number = {9},

pages = {2505--2511},

doi = {10.1016/j.tet.2004.12.061}

}

MLA

Cite this

MLA Copy

Maes, Dominick, et al. “Synthesis and structural revision of naturally occurring ayapin derivatives.” Tetrahedron, vol. 61, no. 9, Feb. 2005, pp. 2505-2511. https://doi.org/10.1016/j.tet.2004.12.061.

Publisher

Elsevier

Journal

Tetrahedron

scimago Q3

wos Q2

SJR

0.426

CiteScore

4.1

Impact factor

2.2

ISSN

00404020 (Print)

14645416 (Electronic)