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Publications - Bioorganic Chemistry

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Displaying results 1 to 6 of 6.

Publications

Wessjohann, L. A.; Scheid, G. O.; Eichelberger, U.; Umbreen, S.; Total Synthesis of Epothilone D: The Nerol/Macroaldolization Approach J. Org. Chem. 78, 10588-10595, (2013) DOI: 10.1021/jo401355r

A highly convergent and stereocontrolled synthesis of epothilone D (4) is reported. Key features are a cheap and Z-selective synthesis of the northern half based on nerol and acetoacetate and chromium(II)-mediated Reformatsky reactions as a powerful tool for chemoselective asymmetric carbon–carbon bond formations, including an unusual stereospecific macroaldolization.
Publications

Dömling, A.; Beck, B.; Eichelberger, U.; Sakamuri, S.; Menon, S.; Chen, Q.-Z.; Lu, Y.; Wessjohann, L.; Corrigendum: Total Synthesis of Tubulysin U and V Angew. Chem. Int. Ed. 46, 2347-2348, (2007) DOI: 10.1002/anie.200790053

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Publications

Dömling, A.; Beck, B.; Eichelberger, U.; Sakamuri, S.; Menon, S.; Chen, Q.-Z.; Lu, Y.; Wessjohann, L.; Berichtigung: Total Synthesis of Tubulysin U and V Angew. Chem. 119, 2399-2400, (2007) DOI: 10.1002/ange.200790053

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Publications

Dömling, A.; Beck, B.; Eichelberger, U.; Sakamuri, S.; Menon, S.; Chen, Q.-Z.; Lu, Y.; Wessjohann, L. A.; Total Synthesis of Tubulysin U and V Angew. Chem. Int. Ed. 45, 7235-7239, (2006) DOI: 10.1002/anie.200601259

Tubulysins are among the most potent cytotoxic agents known. Now the first total synthesis of some members has been achieved by utilizing a rapid three‐component reaction for the synthesis of the unusual central thiazole amino acid tubuvaline (see scheme; Boc=tert ‐butoxycarbonyl, Ac=acetyl), thereby opening new perspectives for anticancer drug development.
Publications

Dömling, A.; Beck, B.; Eichelberger, U.; Sakamuri, S.; Menon, S.; Chen, Q.-Z.; Lu, Y.; Wessjohann, L. A.; Total Synthesis of Tubulysin U and V Angew. Chem. 118, 7393-7397, (2006) DOI: 10.1002/ange.200601259

Tubulysine gehören zu den wirksamsten bekannten Zytostatika. Die erste Totalsynthese einiger Vertreter gelang mit einer schnellen Dreikomponenten‐Eintopfsynthese der ungewöhnlichen zentralen Thiazol‐Aminosäure Tubuvalin (siehe Schema; Boc=tert ‐Butoxycarbonyl, Ac=Acetyl) und eröffnet neue Perspektiven in der Anwendung als Wirkstoff.
Publications

Richter, W. G.; Cappi, M. W.; Henkel, B.; Hess, S.; Surivet, J. P.; Baeschlin, D.; Hubschwerlen, C.; Höfle, G.; Wessjohann, L. A.; Eichelberger, U.; Second generation epothilones and their biological properties Clin. Cancer Res. 9, 6137, (2003)

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