Friday, January 20, 2017

Uses for Akanocure Stereotetrad Lactones 1b: lactone openings with oxygen nucleophiles


One of PolySciTech’s latest product offerings is Akanocure stereotetrad lactones (https://akinainc.com/polyscitech/products/akanocure/index.php) for use as synthetic precursors. There are many potential reactions for these lactones which can result in a wide array of useful molecules. In this series of postings, we will highlight potential uses of these materials. One of the uses is to open the lactone ring utilizing an oxygen nucleophile. This reaction has been successfully applied towards the generation of (+)-Neopeltolide, a promising cytostatic, anti-proliferative macrolide which has a broad range of activity against cancerous cells. The chemical was originally isolated from a deep-water sponges and is very difficult to source naturally in usable quantities. This research usage holds promise for commercial scale synthesis of chemotherapeutic reagents that are difficult to extract from natural resources. You can read more about this application here: Guinchard, Xavier, and Emmanuel Roulland. "Total synthesis of the antiproliferative macrolide (+)-neopeltolide." Organic letters 11, no. 20 (2009): 4700-4703. http://pubs.acs.org/doi/abs/10.1021/ol902047z?journalCode=orlef7&quickLinkVolume=11&quickLinkPage=4700&selectedTab=citation&volume=11

“A concise total synthesis of the very promising antiproliferative macrolide (+)-neopeltolide (1) has been performed in 16 steps. The main steps of this approach are a RuII-catalyzed alkyne−enal coupling, a Pd0-catalyzed desulfurative cross-coupling, and a stereoselective InIII-catalyzed propargylation. Four stereogenic centers out of six have been set thanks to substrate-controlled diastereoselective reactions with minimal reliance on protecting groups.”
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