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同问

有机化学，药物化学或化学生物学

Research Topic for the ParisTech/CSC PhD Program
Subfield: Organic chemistry
ParisTech School: Ecole Polytechnique
Title: Combining biomimetic and diversity-oriented strategies to synthesize natural products and medicinally relevant analogues in the aurachin series
Advisor(s):
Dr. Bastien Nay, bastien.nay@polytechnique.edu, https://naygroup.wordpress.com/
Short description of possible research topics for a PhD:
In 2013 we described the first total synthesis of aurachin D and analogues, and found potent inhibitory properties on the mitochondrial respiratory chain.1 Based on Müller's biosynthetic hypotheses, we also investigated the reactivity of our aurachin analogues in the presence of one of the aurachin biosynthetic enzymes, leading to new biosynthetic hypotheses involving a cascade of retro-[2,3]Wittig and Claisen rearrangements instead of the originally suggested pinacol rearrangement.2 Based on these findings, this PhD project aims at developing bio-inspired strategies to synthesize aurachins B and C. Diversity-oriented and function-oriented strategies will be applied in order to (1) build a medicinally relevant library of compounds and test it on relevant biological targets, and (2) simplify the aurachin core to the essential elements for biological activities (e.g. a shorter geranyl derivative has the same activity as the original farnesyl). In addition, a final level of diversity (and complexity) will be obtained through bio-inspired photooxygenated processes currently developed in our group. Overall the methodological aspects of organic synthesis will gain from our biosynthetic hypothesis to be synthetically challenged, since unprecedented chemical rearrangements (i.e. retro-[2,3]Wittig) with potentially high impact are expected to be unveiled by this work.
Required background of the student: The PhD applicant should have a Master degree in organic chemistry and a strong interest in organic synthesis and synthetic methodologies. A high level of spoken and written English is also expected. An interest in biosynthetic pathways and chemical biology would be appreciated，

只要csc？