Studies on C18–C20 Aldol Couplings of Rhizopodin

Michael Dieckmann; Sven Rudolph; Carolin Lang; Wiebke Ahlbrecht; Dirk Menche

doi:10.1055/s-0033-1338493

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(16): 2305-2315
DOI: 10.1055/s-0033-1338493

paper

Studies on C18–C20 Aldol Couplings of Rhizopodin

Michael Dieckmann

^aKekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany Fax: +49(228)735813 eMail: dirk.menche@uni-bonn.de

,

Sven Rudolph

^bASM Research Chemicals, 30938 Burgwedel, Germany

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Carolin Lang

^cUniversität Heidelberg, Institut für Organische Chemie, INF 270, 69120 Heidelberg, Germany

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Wiebke Ahlbrecht

^cUniversität Heidelberg, Institut für Organische Chemie, INF 270, 69120 Heidelberg, Germany

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Dirk Menche*

^aKekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany Fax: +49(228)735813 eMail: dirk.menche@uni-bonn.de

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Abstract

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Abstract

The aldol addition of an enol(ate) to a carbonyl compound is one of the most powerful and versatile C–C bond forming reactions. In complex target synthesis the coupling of two chiral partners may complicate the stereochemical outcome by multiple stereoinductions. Here, we report studies on pivotal aldol couplings employed in the rhizopodin synthesis, detailing the various directing effects exerted by the stereogenic centers present in this sterically hindered connection.

Key words

natural products - aldol reaction - asymmetric synthesis - methyl ketone - Felkin product

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Referenzen

References

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