Towards the total synthesis of tonantzitlolone - Preparation of key fragments and the complete carbon backbone

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OriginalspracheEnglisch
Seiten (von - bis)4457-4460
Seitenumfang4
FachzeitschriftTetrahedron Letters
Jahrgang45
Ausgabenummer23
PublikationsstatusVeröffentlicht - 6 Mai 2004

Abstract

The first synthetic advances towards the novel diterpenoid tonantzitlolone 1 are described. The key steps in the synthesis involve a chromium(II) Reformatsky reaction, a diastereoselective C1 extension and an expeditious aldol coupling step of two advanced precursors.

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Towards the total synthesis of tonantzitlolone - Preparation of key fragments and the complete carbon backbone. / Wittenberg, Rüdiger; Beier, Christian; Dräger, Gerald et al.
in: Tetrahedron Letters, Jahrgang 45, Nr. 23, 06.05.2004, S. 4457-4460.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Wittenberg R, Beier C, Dräger G, Jas G, Jasper C, Monenschein H et al. Towards the total synthesis of tonantzitlolone - Preparation of key fragments and the complete carbon backbone. Tetrahedron Letters. 2004 Mai 6;45(23):4457-4460. doi: 10.1016/j.tetlet.2004.04.056
Wittenberg, Rüdiger ; Beier, Christian ; Dräger, Gerald et al. / Towards the total synthesis of tonantzitlolone - Preparation of key fragments and the complete carbon backbone. in: Tetrahedron Letters. 2004 ; Jahrgang 45, Nr. 23. S. 4457-4460.
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abstract = "The first synthetic advances towards the novel diterpenoid tonantzitlolone 1 are described. The key steps in the synthesis involve a chromium(II) Reformatsky reaction, a diastereoselective C1 extension and an expeditious aldol coupling step of two advanced precursors.",
keywords = "Chromium Reformatsky reaction, Formylation, Polymer-supported reagents, Terpene, Total synthesis",
author = "R{\"u}diger Wittenberg and Christian Beier and Gerald Dr{\"a}ger and Gerhard Jas and Christian Jasper and Holger Monenschein and Andreas Kirschning",
note = "Funding information: This research was supported by a graduate fellowship provided by the state of Lower Saxony for R.W. and by a Kekul{\'e} scholarship for C.J. provided by the Stiftung Stipendien-Fonds des Verbandes der Chemischen Industrie. We are grateful to Dr. Jasmin Jakupovic (AnalytiCon Discovery GmbH, Potsdam) for providing us with details on Tonantzitlolone. Finally, we thank the Fonds der Chemischen Industrie for general support.",
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AU - Wittenberg, Rüdiger

AU - Beier, Christian

AU - Dräger, Gerald

AU - Jas, Gerhard

AU - Jasper, Christian

AU - Monenschein, Holger

AU - Kirschning, Andreas

N1 - Funding information: This research was supported by a graduate fellowship provided by the state of Lower Saxony for R.W. and by a Kekulé scholarship for C.J. provided by the Stiftung Stipendien-Fonds des Verbandes der Chemischen Industrie. We are grateful to Dr. Jasmin Jakupovic (AnalytiCon Discovery GmbH, Potsdam) for providing us with details on Tonantzitlolone. Finally, we thank the Fonds der Chemischen Industrie for general support.

PY - 2004/5/6

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N2 - The first synthetic advances towards the novel diterpenoid tonantzitlolone 1 are described. The key steps in the synthesis involve a chromium(II) Reformatsky reaction, a diastereoselective C1 extension and an expeditious aldol coupling step of two advanced precursors.

AB - The first synthetic advances towards the novel diterpenoid tonantzitlolone 1 are described. The key steps in the synthesis involve a chromium(II) Reformatsky reaction, a diastereoselective C1 extension and an expeditious aldol coupling step of two advanced precursors.

KW - Chromium Reformatsky reaction

KW - Formylation

KW - Polymer-supported reagents

KW - Terpene

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DO - 10.1016/j.tetlet.2004.04.056

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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