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Total synthesis of vancomycin, parts 1-4 (RSC Publishing)

Total synthesis of vancomycin, parts 1-4

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Total Synthesis of Vancomycin—Part 4: Attachment of …

Vancomycin is the last line of defense available in the clinic for treating multidrug-resistant bacterial infections. Vancomycin contains two 16-membered diaryl ether macrocycles, each of which contains a stereogenic axis across the diaryl ether linkage. Since an effective total synthesis of vancomycin requires that these stereogenic axes be formed in a stereoselective manner, we have developed an atropselective variation of the triazene mediated diaryl ether forming reaction. This variation introduced an energetic penalty into the transition state of the undesired atropisomer. This reaction is used to synthesize the C−O−D diaryl ether macrocycle found in vancomycin with high diastereoselectivity (de > 90%), providing the naturally occurring atropisomeric configuration.

Total Synthesis of Vancomycin—Part 4: ..

Research in our group focuses on the chemical synthesis and chemical biology of natural and designed compounds. Programs are directed toward the discovery and invention of new synthetic reactions and the development of novel synthetic strategies for the synthesis of complex molecules. Additional aspects of the work include investigations of the biological properties of the synthesized molecules and of the mechanism of action of biologically active compounds, as well as drug design and development.Specific examples of our past and present projects include the total synthesis of calicheamicin γ1I, (Mylotarg®, anticancer drug), Taxol® (anticancer drug), the epothilones (anticancer agents), brevetoxins A and B, azaspiracids 1−3 and maitotoxin (marine neurotoxins), vancomycin, thiostrepton, abyssomycin, platensimycin, the hirsutellones (antibiotics) and the biyouyanagins (antiviral agents).Overall, our research programs aim to advance the field of total synthesis and to apply the fundamental knowledge gained to the drug discovery and development process. Education of the next generation of young scientists in the chemical and biological sciences is our other top priority.For more information on our educational and research activities, see our webpage:

Total Synthesis of Vancomycin—Part 4: Attachment ..

Specific examples of our past and present projects include the total synthesis of calicheamicin γ1I, (Mylotarg®, anticancer drug), Taxol® (anticancer drug), the epothilones (anticancer agents), brevetoxins A and B, azaspiracids 1−3 and maitotoxin (marine neurotoxins), vancomycin, thiostrepton, abyssomycin, platensimycin, the hirsutellones (antibiotics) and the biyouyanagins (antiviral agents).

Sequential attachment of the required sugar moieties onto a suitably protected aglycon derivative, followed by deprotection, allowed the stereoselective total synthesis of the glycopeptide antibiotic vancomycin (1).

Synthesis, Evaluation, 2016, 398-438 ..

Full details of a diastereoselective total synthesis of the vancomycin aglycon are described. Two key aromatic nucleophilic substitution macrocyclizations with formation of the 16-membered diaryl ethers were enlisted for sequential CD and DE ring formations, an effective macrolactamization was developed for closure of the 12-membered biaryl AB ring system, and the defined order of CD, AB, and DE ring closures permitted selective thermal atropisomerism of the newly formed ring systems or their immediate precursors. This indirect control of the atropisomer stereochemistry allowed all synthetic material to be funneled into the one of eight atropdiastereomers characterizing the natural product.

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  • Synthesis of the ABC Ring of Paclitaxel by SmI ..

    such as the triazene-driven biaryl ether synthesis, have been developed during the total synthesis of vancomycin (1).

  • Total Synthesis of the Vancomycin Aglycon - Journal of …

    17/07/2010 · "Total Syntheses of Vancomycin and ..

  • Click Chemistry -- Publications

    Abstract

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