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DC Field | Value | Language |
---|---|---|
dc.contributor.author | Höck, Stefan | - |
dc.contributor.author | Koch, Florian | - |
dc.contributor.author | Borschberg, Hans-Jürg | - |
dc.date.accessioned | 2018-10-19T14:27:47Z | - |
dc.date.available | 2018-10-19T14:27:47Z | - |
dc.date.issued | 2004 | - |
dc.identifier.issn | 0957-4166 | de_CH |
dc.identifier.issn | 1362-511X | de_CH |
dc.identifier.uri | https://digitalcollection.zhaw.ch/handle/11475/11998 | - |
dc.description.abstract | The synthesis of the isoquinuclidine core of the Iboga alkaloid family is described. This building block contains the entire stereochemical information of the targeted natural products. Starting with (S)-4-(hydroxymethyl)-4-butanolide, a derivative available in two steps from l-glutamate, (S)-4-benzyloxy-5,5-dimethoxypentanoic acid was obtained in four steps. Mitsunobu esterification with (S)-but-3-en-2-ol furnished the inverted ester, which was then subjected to an Ireland–Claisen rearrangement. This crucial step took place with a very satisfactory chirality transfer from the alcohol component to the new carbon backbone of the product. After transformation of the resulting silyl ester function into a hydroxylamino group, the dimethyl acetal moiety was hydrolyzed with 3 M sulfuric acid at 47°C. Under these conditions, the resulting cyclic nitrone could not be isolated, because it underwent a rapid intramolecular nitrone–olefin [3+2]-cycloaddition reaction to furnish the expected tricyclic isoxazolidine derivative in 67% yield. After chromatographic purification, this product was obtained enantiomerically pure and with a chemical purity of 96%. The targeted isoquinuclidine building block was thus obtained from (S)-4-(hydroxymethyl)-4-butanolide in 13 steps with an overall yield of 9.2%, which amounts to an average yield of 83.3% per step. | de_CH |
dc.language.iso | en | de_CH |
dc.publisher | Elsevier | de_CH |
dc.relation.ispartof | Tetrahedron: Asymmetry | de_CH |
dc.rights | Licence according to publishing contract | de_CH |
dc.subject | Indole alkaloids | de_CH |
dc.subject | Chirality transfer | de_CH |
dc.subject | Ireland-Claisen rearrangemenent | de_CH |
dc.subject.ddc | 572: Biochemie | de_CH |
dc.title | Chirality transfer in an Ireland-Claisen rearrangement : a new approach toward the Iboga alkaloids | de_CH |
dc.type | Beitrag in wissenschaftlicher Zeitschrift | de_CH |
dcterms.type | Text | de_CH |
zhaw.departement | Life Sciences und Facility Management | de_CH |
zhaw.organisationalunit | Institut für Chemie und Biotechnologie (ICBT) | de_CH |
dc.identifier.doi | 10.1016/j.tetasy.2004.04.028 | de_CH |
zhaw.funding.eu | No | de_CH |
zhaw.issue | 11 | de_CH |
zhaw.originated.zhaw | No | de_CH |
zhaw.pages.end | 1808 | de_CH |
zhaw.pages.start | 1801 | de_CH |
zhaw.publication.status | publishedVersion | de_CH |
zhaw.volume | 15 | de_CH |
zhaw.publication.review | Peer review (Publikation) | de_CH |
Appears in collections: | Publikationen Life Sciences und Facility Management |
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Höck, S., Koch, F., & Borschberg, H.-J. (2004). Chirality transfer in an Ireland-Claisen rearrangement : a new approach toward the Iboga alkaloids. Tetrahedron: Asymmetry, 15(11), 1801–1808. https://doi.org/10.1016/j.tetasy.2004.04.028
Höck, S., Koch, F. and Borschberg, H.-J. (2004) ‘Chirality transfer in an Ireland-Claisen rearrangement : a new approach toward the Iboga alkaloids’, Tetrahedron: Asymmetry, 15(11), pp. 1801–1808. Available at: https://doi.org/10.1016/j.tetasy.2004.04.028.
S. Höck, F. Koch, and H.-J. Borschberg, “Chirality transfer in an Ireland-Claisen rearrangement : a new approach toward the Iboga alkaloids,” Tetrahedron: Asymmetry, vol. 15, no. 11, pp. 1801–1808, 2004, doi: 10.1016/j.tetasy.2004.04.028.
HÖCK, Stefan, Florian KOCH und Hans-Jürg BORSCHBERG, 2004. Chirality transfer in an Ireland-Claisen rearrangement : a new approach toward the Iboga alkaloids. Tetrahedron: Asymmetry. 2004. Bd. 15, Nr. 11, S. 1801–1808. DOI 10.1016/j.tetasy.2004.04.028
Höck, Stefan, Florian Koch, and Hans-Jürg Borschberg. 2004. “Chirality Transfer in an Ireland-Claisen Rearrangement : A New Approach toward the Iboga Alkaloids.” Tetrahedron: Asymmetry 15 (11): 1801–8. https://doi.org/10.1016/j.tetasy.2004.04.028.
Höck, Stefan, et al. “Chirality Transfer in an Ireland-Claisen Rearrangement : A New Approach toward the Iboga Alkaloids.” Tetrahedron: Asymmetry, vol. 15, no. 11, 2004, pp. 1801–8, https://doi.org/10.1016/j.tetasy.2004.04.028.
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