Synthesis of the B-seco limonoid core scaffold
Synthetic investigations towards the structurally complex and highly decorated framework of B-seco limonoid natural products by means of a [3,3]-sigmatropic rearrangement are described. Detailed model studies reveal, that an Ireland–Claisen rearrangement can be employed to construct the central C9–C...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2014-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.15 |
| _version_ | 1818657481054748672 |
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| author | Hanna Bruss Hannah Schuster Rémi Martinez Markus Kaiser Andrey P. Antonchick Herbert Waldmann |
| author_facet | Hanna Bruss Hannah Schuster Rémi Martinez Markus Kaiser Andrey P. Antonchick Herbert Waldmann |
| author_sort | Hanna Bruss |
| collection | DOAJ |
| description | Synthetic investigations towards the structurally complex and highly decorated framework of B-seco limonoid natural products by means of a [3,3]-sigmatropic rearrangement are described. Detailed model studies reveal, that an Ireland–Claisen rearrangement can be employed to construct the central C9–C10 bond thereby giving access to the B-seco limonoid scaffold. However, application of the developed strategy ended up failing in more complex and sterically demanding systems. |
| first_indexed | 2024-12-17T03:42:10Z |
| format | Article |
| id | doaj.art-57fa4f58a2ea4b78855a8dfda4506241 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T03:42:10Z |
| publishDate | 2014-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-57fa4f58a2ea4b78855a8dfda45062412022-12-21T22:04:59ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-01-0110119420810.3762/bjoc.10.151860-5397-10-15Synthesis of the B-seco limonoid core scaffoldHanna Bruss0Hannah Schuster1Rémi Martinez2Markus Kaiser3Andrey P. Antonchick4Herbert Waldmann5Abteilung Chemische Biologie, Max-Planck-Institut für Molekulare Physiologie, Otto-Hahn-Straße 11, 44227 Dortmund, GermanyAbteilung Chemische Biologie, Max-Planck-Institut für Molekulare Physiologie, Otto-Hahn-Straße 11, 44227 Dortmund, GermanyAbteilung Chemische Biologie, Max-Planck-Institut für Molekulare Physiologie, Otto-Hahn-Straße 11, 44227 Dortmund, GermanyChemical Biology, Zentrum für Medizinische Biotechnologie, Fakultät für Biologie, Universität Duisburg-Essen, Universitätsstraße 2, 45117 Essen, GermanyAbteilung Chemische Biologie, Max-Planck-Institut für Molekulare Physiologie, Otto-Hahn-Straße 11, 44227 Dortmund, GermanyAbteilung Chemische Biologie, Max-Planck-Institut für Molekulare Physiologie, Otto-Hahn-Straße 11, 44227 Dortmund, GermanySynthetic investigations towards the structurally complex and highly decorated framework of B-seco limonoid natural products by means of a [3,3]-sigmatropic rearrangement are described. Detailed model studies reveal, that an Ireland–Claisen rearrangement can be employed to construct the central C9–C10 bond thereby giving access to the B-seco limonoid scaffold. However, application of the developed strategy ended up failing in more complex and sterically demanding systems.https://doi.org/10.3762/bjoc.10.15B-seco limonoidsbiology oriented synthesisIreland–Claisen rearrangementnatural productstetranortriterpenoids |
| spellingShingle | Hanna Bruss Hannah Schuster Rémi Martinez Markus Kaiser Andrey P. Antonchick Herbert Waldmann Synthesis of the B-seco limonoid core scaffold Beilstein Journal of Organic Chemistry B-seco limonoids biology oriented synthesis Ireland–Claisen rearrangement natural products tetranortriterpenoids |
| title | Synthesis of the B-seco limonoid core scaffold |
| title_full | Synthesis of the B-seco limonoid core scaffold |
| title_fullStr | Synthesis of the B-seco limonoid core scaffold |
| title_full_unstemmed | Synthesis of the B-seco limonoid core scaffold |
| title_short | Synthesis of the B-seco limonoid core scaffold |
| title_sort | synthesis of the b seco limonoid core scaffold |
| topic | B-seco limonoids biology oriented synthesis Ireland–Claisen rearrangement natural products tetranortriterpenoids |
| url | https://doi.org/10.3762/bjoc.10.15 |
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