A flow process for the multi-step synthesis of the alkaloid natural product oxomaritidine: a new paradigm for molecular assembly

Baxendale, Ian R.; Deeley, Jon; Griffiths‐Jones, Charlotte M.; Ley, Steven V.; Saaby, Steen; Tranmer, Geoffrey K.

doi:10.1039/b600382f

Cited by 321 publications

(189 citation statements)

References 23 publications

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“…43 The multistep synthesis targeted the alkaloid natural product (AE)-oxomaritidine 63 and relied on various packed columns containing immobilised reagents, catalysts, scavengers or catch and release agents. The synthesis started with formation of azide 56 from benzyl bromide 55 which was followed by the formation of an azaWittig intermediate trapped on the supported material.…”

Section: Issue 8: Flow and Photochemistry-new Optionsmentioning

confidence: 99%

Ten key issues in modern flow chemistry

2011

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He studied chemistry at the Leibniz University Hannover where he received his diploma degree in 2008. He is currently performing his doctoral studies at Hannover under the supervision of Prof. Andreas Kirschning with the aid of a scholarship by the Fonds der Chemischen Industrie. In 2010 he spent several months in the group of Prof. S. V. Ley at Cambridge University (UK). His research is focussed on the development of an inductively heated micro flow system for organic synthesis.A key aspect of his work is the implementation of a multistep reaction and an immobilised catalyst into micro flow systems. Sascha Ceylan (right) was born in Augsburg, Germany, in 1981 and studied chemistry at Leibniz University Hannover and at Imperial College London under the guidance of Prof. A. G. M. Barrett (UK). He received his diploma degree in 2007 and thereafter began his doctoral studies in Hannover under the supervision of Prof. A. Kirschning. Following a research stay at the University of Hong Kong (Prof. P. Toy) he received his PhD early 2011. His scientific interest focuses on developing micro flow systems, especially inductively heated reactors, and investigations on palladium catalysed Umpolung reactions. Andreas Kirschning studied chemistry at the University of Hamburg and Southampton University (UK). In Hamburg, he joined the group of Prof. E. Schaumann and received his PhD in 1989 working in the field of organosilicon chemistry. After a postdoctoral stay at the University of Washington (Seattle, USA) with Prof. H. G. Floss, supported by a Feodor-Lynen scholarship of the Alexander-von Humboldt foundation, he started his independent research at the Clausthal University of Technology in 1991, where he finished his habilitation in 1996. In 2000 he moved to the Leibniz University Hannover and became a director of the institute of organic chemistry. He is one of the editors of RO ¨MPP online, Natural Products Reports and The Beilstein Journal of Organic Chemistry. His research interests cover structure elucidation as well as the total synthesis and mutasynthesis of natural products, biomedical biopolymers, and synthetic technology (solid-phase assisted synthesis, microreactors, inductive heating).

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Section: Issue 8: Flow and Photochemistry-new Optionsmentioning

confidence: 99%

Ten key issues in modern flow chemistry

2011

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“…The crude intermediate was re-dissolved in DCM, which was also useful to avoid working with highly diluted mixtures in the final steps. 26 THF was exchanged to acetonitrile using a nebulizing evaporator device to avoid polymerization side reaction under the acidic conditions of the next step in course of the synthesis of 2-aminoadamantane-2-carboxylic acid. 27 Reactivity can be fine-tuned by slight modification of the solvent system by addition or removal of cosolvents.…”

Section: Choosing Appropriate Solventsmentioning

confidence: 99%

“…Hydrogen is commonly used in flow synthesis, 99,100 usually in excess amounts. When hydrogenation is followed by other steps, 9,26,29,33,101,102 a simple buffer flask allows the outgassing of hydrogen, after the pressure is reduced. However, in some cases the applied chemistry did not tolerate this method.…”

Section: In-line Work-upmentioning

confidence: 99%

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The route from problem to solution in multistep continuous flow synthesis of pharmaceutical compounds

Bana

Örkényi

Lövei

et al. 2017

Bioorganic & Medicinal Chemistry

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a b s t r a c tRecent advances in the field of continuous flow chemistry allow the multistep preparation of complex molecules such as APIs (Active Pharmaceutical Ingredients) in a telescoped manner. Numerous examples of laboratory-scale applications are described, which are pointing towards novel manufacturing processes of pharmaceutical compounds, in accordance with recent regulatory, economical and quality guidances. The chemical and technical knowledge gained during these studies is considerable; nevertheless, connecting several individual chemical transformations and the attached analytics and purification holds hidden traps. In this review, we summarize innovative solutions for these challenges, in order to benefit chemists aiming to exploit flow chemistry systems for the synthesis of biologically active molecules.

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“…7). Accordingly, the synthesis of (±)-Oxomaritidine is described and a series of fixed bed reactors optimised accordingly [55,58] (Fig. 8).…”

Section: -Multistep Integrated Modulesmentioning

confidence: 99%

Continuous flow (micro-)reactors for heterogeneously catalyzed reactions: Main design and modelling issues

Rossetti

2018

Catalysis Today

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A flow process for the multi-step synthesis of the alkaloid natural product oxomaritidine: a new paradigm for molecular assembly

Cited by 321 publications

References 23 publications

Ten key issues in modern flow chemistry

Ten key issues in modern flow chemistry

The route from problem to solution in multistep continuous flow synthesis of pharmaceutical compounds

Continuous flow (micro-)reactors for heterogeneously catalyzed reactions: Main design and modelling issues

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