Uses for Akanocure Stereotetrad Lactones 2b: lactone openings with primary nitrogen 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 usage is opening the lactone ring utilizing primary nitrogens (amines). This method has been utilized to generate rhizopodin, a myxobacterial metabolite which is a potent actin-binding chemotherapeutic agent. This research holds promise for improved availability of effective chemotherapy agents. Read more: Dieckmann, Michael, Manuel Kretschmer, Pengfei Li, Sven Rudolph, Daniel Herkommer, and Dirk Menche. "Total synthesis of rhizopodin." Angewandte Chemie International Edition 51, no. 23 (2012): 5667-5670. http://onlinelibrary.wiley.com/doi/10.1002/anie.201301978/full

“The total synthesis of the myxobacterial metabolite rhizopodin, a potent actin-binding anticancer agent, has been achieved. The modular synthesis utilizes a common C1–C22 monomeric unit to assemble the dimeric 38-membered macrodiolide core, which was elaborated by a bidirectional boron-mediated aldol reaction to install the characteristic side-chains. The final global deprotection was critically dependent on the correct choice of silyl protecting groups at C16/C16′.”