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dc.contributor.authorHöck, Stefan-
dc.contributor.authorKoch, Florian-
dc.contributor.authorBorschberg, Hans-Jürg-
dc.date.accessioned2018-10-19T14:27:47Z-
dc.date.available2018-10-19T14:27:47Z-
dc.date.issued2004-
dc.identifier.issn0957-4166de_CH
dc.identifier.issn1362-511Xde_CH
dc.identifier.urihttps://digitalcollection.zhaw.ch/handle/11475/11998-
dc.description.abstractThe 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.isoende_CH
dc.publisherElsevierde_CH
dc.relation.ispartofTetrahedron: Asymmetryde_CH
dc.rightsLicence according to publishing contractde_CH
dc.subjectIndole alkaloidsde_CH
dc.subjectChirality transferde_CH
dc.subjectIreland-Claisen rearrangemenentde_CH
dc.subject.ddc572: Biochemiede_CH
dc.titleChirality transfer in an Ireland-Claisen rearrangement : a new approach toward the Iboga alkaloidsde_CH
dc.typeBeitrag in wissenschaftlicher Zeitschriftde_CH
dcterms.typeTextde_CH
zhaw.departementLife Sciences und Facility Managementde_CH
zhaw.organisationalunitInstitut für Chemie und Biotechnologie (ICBT)de_CH
dc.identifier.doi10.1016/j.tetasy.2004.04.028de_CH
zhaw.funding.euNode_CH
zhaw.issue11de_CH
zhaw.originated.zhawNode_CH
zhaw.pages.end1808de_CH
zhaw.pages.start1801de_CH
zhaw.publication.statuspublishedVersionde_CH
zhaw.volume15de_CH
zhaw.publication.reviewPeer 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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