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University of Groningen

Total synthesis of mycolic acids and site-selective functionalization of aminoglycoside

antibiotics

Tahiri, Nabil

IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below.

Document Version

Publisher's PDF, also known as Version of record

Publication date: 2019

Link to publication in University of Groningen/UMCG research database

Citation for published version (APA):

Tahiri, N. (2019). Total synthesis of mycolic acids and site-selective functionalization of aminoglycoside antibiotics. University of Groningen.

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Stellingen

behorende bij het proefschrift

Total Synthesis of Mycolic Acids and Site-selective Functionalization of Aminoglycoside

Antibiotics

Nabil Tahiri

1. Synthetic and natural samples with superimposable NMR spectra are not necessarily identical! This thesis

2. Pentane/acetonitrile extraction is a valuable method in lipid synthesis.

3. The Swern oxidation of enantiopure solketal is problematic, and results in erosion of ee.

M. Suzuki, H. Koyano, R. Noyori, H. Hashimoto, M. Negishi, A. Ichikawa, S. Ito, Tetrahedron 1992, 48, 2635–2658

M. D. Lebar, B. J. Baker, Tetrahedron Lett. 2007, 48, 8009–8010

4. Journals should demand the Glorius functional group compatibility test on top of the usual substrate scope table for methodology papers.

K.D. Collins, F. Glorius Nat. Chem. 2013, 597-601

T. Gensch,M. Teders, F Glorius, J. Org. Chem. 2017, 82, 9154−9159

5. An excellent chemist is able to spot opportunities in unexpected reaction outcomes.

6. Not depicting reaction steps, how trivial they may seem, does not contribute to the readability of a total synthesis paper.

J. R. Al Dulayymi, M. S. Baird, E. Roberts, M. Deysel, J. Verschoor, Tetrahedron 2007, 63, 2571–2592 7. Chemical modification of the 3’-OH in Neomycin is required but not sufficient to overcome bacterial

resistance caused by the enzyme APH(3’)IIIa

P. R. Thompson, D. W. Hughes, G. D. Wright, Biochemistry 1996, 35, 8686-8695 8. Being a loyal and unquestioning follower of anything is wrong!

9. Technology has provided great convenience at the cost of a small amount of privacy, but in the future a small amount of privacy will come at the cost of a lot of convenience.

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