Synthetic methods enabling biological studies. A journey from the synthesis of ring-expanded carbohydrates, phosphine catalysis to development of bio-reductive pro-drugs for cancer

<strong>Seminar of the School of Physical Sciences -------------------------------------------------</strong> Title: <strong>Synthetic methods enabling biological studies. A journey from the synthesis of ring-expanded carbohydrates, phosphine catalysis to development of bio-reductive pro-drugs for cancer</strong> Speaker: <strong>Jaideep Saha</strong> (University of Oxford, Oxford) Date:<strong> September 16, 2015 </strong> <strong>Abstract: T</strong>he first part of the talk will focus on the synthesis and reactivity of novel ring-expanded septanose-carbohydrates (seven membered oxacycles). Their development is inspired from seven-membered iminoalditols (azepanes), which have found tremendous applications as glycosidase inhibitors. Septanose carbohydrates are considered as flexible-mimetics of natural sugars and we have used them as a tool to study biological processes. In our study, an acid mediated tandem cyclization-glycosylation route is developed for the asymmetric synthesis of ring-expanded analogues of amino sugars. Broader investigations have followed towards the preparation of novel seven-membered amino glycosides and their incorporation into natural product-like frameworks. The second half of my talk will detail about a novel phosphine-catalyzed tandem cycloisomerization/ hetero Diels-Alder process for the preparation of highly functionalized spiroketal/ dihydropyrazole scaffolds and the development of bioreductive prodrugs based on Chk1 inhibitor for hypoxic tumor cells and subsequent challenges in the development will also be discussed.