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Application of DNA-based asymmetric catalysis to natural product synthesis

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  • Full or part time
    Dr Stellios Arseniyadis
  • Application Deadline
    Applications accepted all year round
  • Competition Funded PhD Project (Students Worldwide)
    Competition Funded PhD Project (Students Worldwide)

Project Description

The Arseniyadis group is principally interested in developing new synthetic tools to attain high structural and functional complexity. These methods lie within the areas of organocatalysis, transition metal catalysis and natural product synthesis. Over the years, the group was thus able to develop several new reactions, which were used as key steps in the total synthesis of various natural products including (-)-pironetin, cystothiazole A and F, melithiazoles A, C, G and H, myxothiazole Z, (-)-bitungolide F, acremolide B, (-)-nephrosteranic acid, (-)-roccellaric acid, lyngbouilloside aglycon and leustroducsin B. More recently, the group also got involved in the development of new DNA-based bio-hybrid catalysts. In this context, we recently reported the first example of a left-helical enantioselective induction using L-nucleic acids that allowed a reliable and predictable access to both enantiomers for a given reaction (see Angew. Chem. Int. Ed. 2013, 52, 11546-11549). We also reported a fully recyclable cellulose-supported DNA-based catalyst that offers high levels of enantioselectivity on various Cu(II)-catalyzed asymmetric reactions including Friedel-Crafts alkylations and Michael additions. Most importantly, this supported biohybrid catalyst could be implemented to a single-pass, continuous-flow process allowing to perform reactions on more synthetically useful scales (see Chem. Commun. 2015, 51, 6076-6079).

In the present project, we envision to expend the scope of DNA-based asymmetric catalysis by developing new synthetic transformations with a special emphasis given to asymmetric electrocyclization and cycloaddition processes. Most importantly, we wish to apply these methods to the synthesis of various relevent natural products.

Candidates are expected to have a strong background and interest in synthetic organic chemistry. Prior experience in catalysis and multi-step synthesis is desirable but not required as the expertise of the group will provide an ideal training environment.

Please contact Dr Stellios Arseniyadis for more information.
To apply, use the link provided for an online application and send a complete CV and a cover letter outlining your qualifications and previous research experience.

Funding Notes

Applicants wishing to apply for PhD funding through Ciência sem Fronteiras, CONACYT or the China Scholarship Council are welcomed, as are those applicants who can self-fund. Applications are welcome from outstanding students with or expecting to obtain a degree (equivalent to UK 1st or 2:1) in Chemistry. Previous experiences with asymmetric organocatalysis or biocatalysis are desirable but not essential.
Informal enquiries about the project can be made by email to Dr Stellios Arseniyadis ([email protected]).

References

M. Bezagu, S. Arseniyadis, J. Cossy, O. Couture, M. Tanter, F. Monti, P. Tabeling Lab on a Chip 2015, 15, 2025-2029.
E. Benedetti, N. Duchemin, L. Bethge, S. Vonhoff, S. Klussmann, J. J. Vasseur, J. Cossy, M. Smietana, S. Arseniyadis Chem. Commun. 2015, 51, 6076-6079.
M. Bezagu, C. Errico, V. Chaulot-Talmon, F. Monti, M. Tanter, P. Tabeling, J. Cossy, S. Arseniyadis, O. Couture J. Am. Chem. Soc. 2014, 136, 7205-7208.
J. Wang, E. Benedetti, L. Bethge, S. Vonhoff, S. Klussmann, J. J. Vasseur, J. Cossy, M. Smietana, S. Arseniyadis Angew. Chem. Int. Ed. 2013, 52, 11546-11549.
A. Kolleth, M. Cattoen, S. Arseniyadis, J. Cossy Chem. Commun. 2013, 49, 9338-9340.
J. Fournier, O. Lozano, C. Menozzi, S. Arseniyadis, J. Cossy Angew. Chem. Int. Ed. 2013, 52, 1257-1261.
A. Kolleth, S. Christoph, S. Arseniyadis, J. Cossy Chem. Commun. 2012, 48, 10511-10513.
A. Colon, T. J. Hoffman, J. Gebauer, J. Dash, J. H. Rigby, S. Arseniyadis, J. Cossy Chem. Commun. 2012, 48, 10508-10510.
J. Fournier, S. Arseniyadis, J. Cossy Angew. Chem. Int. Ed. 2012, 51, 7562-7566.

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