Hannover, Germany
Hannover, Germany

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Dieckmann M.,University of Heidelberg | Kretschmer M.,University of Heidelberg | Li P.,University of Heidelberg | Li P.,Xi'an Jiaotong University | And 4 more authors.
Angewandte Chemie - International Edition | Year: 2012

Symmetry helps: The total synthesis of the potent actin-targeting C 2-symmetric myxobacterial macrolide rhizopodin (see scheme) is accomplished by the convergent assembly of three building blocks of similar complexity, a concise macrocyclization strategy, and a late-stage introduction of the labile side chains. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Dieckmann M.,University of Heidelberg | Rudolph S.,ASM Research Chemicals | Dreisigacker S.,University of Heidelberg | Menche D.,University of Bonn
Journal of Organic Chemistry | Year: 2012

A highly convergent synthesis of the central dimeric core of the potent antibiotic macrolide rhizopodin is reported. Notable features of the highly concise route include an effective preparation of the key C8-C22 building block based on an iridium-catalyzed Krische allylation and a chemoselective cross-coupling approach toward the macrocycle involving a highly advantageous Heck reaction for macrocyclization. © 2012 American Chemical Society.


Kretschmer M.,University of Heidelberg | Kretschmer M.,Columbia University | Dieckmann M.,University of Bonn | Li P.,University of Heidelberg | And 6 more authors.
Chemistry - A European Journal | Year: 2013

A highly convergent total synthesis of the potent polyketide macrolide rhizopodin has been achieved in 29steps by employing a concise strategy that exploits the molecule′s C2 symmetry. Notable features of this convergent approach include a rapid assembly of the macrocycle through a site-directed sequential cross-coupling strategy and the bidirectional attachment of the side chains by means of Horner-Wadsworth-Emmons (HWE) coupling reactions. During the course of this endeavor, scalable routes for synthesis of three main building blocks of similar complexity were developed that allowed for their stereocontrolled construction. This modular route will be amenable to the development of syntheses of other analogues of rhizopodin. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Dieckmann M.,University of Bonn | Rudolph S.,ASM Research Chemicals | Lang C.,University of Heidelberg | Ahlbrecht W.,University of Heidelberg | Menche D.,University of Bonn
Synthesis (Germany) | Year: 2013

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. © Georg Thieme Verlag Stuttgart. New York.


Kadyrov R.,Evonik Industries | Rosiak A.,Evonik Industries | Rosiak A.,ASM Research Chemicals
Beilstein Journal of Organic Chemistry | Year: 2011

The present work describes the robust synthesis of Ru alkylidene complexes (PCy3)2Cl2Ru=CHR - precursors for metathesis catalysts. Moreover, the dynamic behavior of complexes where R = 2-naphthyl and 2-thienyl was studied. 1H NMR techniques were employed to establish the preferred conformations in solution for both complexes and the energy barrier for rotation around single (Ru=)CH-C(thienyl) bond was estimated (ΔG≠303K = 12.6 kcal/mol).

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