Uses for Akanocure Stereotetrad Lactones 4: lactone openings with sulfur 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 potential reaction is the ring-opening of the lactone using sulfur (thiol) nucleophiles. Recently, this reaction has been applied to the synthesis of peloruside A, a potent chemotherapeutic agent. This research holds promise for improved availability of advanced chemotherapeutic agents. Read more: Raghavan, Sadagopan, and V. Vinoth Kumar. “A stereoselective synthesis of the C9–C19 subunit of (+)-peloruside A.” Organic & biomolecular chemistry 11, no. 17 (2013): 2847-2858. http://pubs.rsc.org/en/content/articlelanding/2013/ob/c3ob27508f#!divAbstract

“Abstract: The stereoselective synthesis of a C9–C19 fragment of the potent antitumor agent peloruside A is disclosed. The C11 stereogenic centre was created by a vinylogous Mukaiyama aldol reaction following Carreira’s protocol, with excellent stereocontrol. The C13 stereogenic centre was introduced by a substrate controlled reduction. The C15 stereocentre was fashioned using Noyori’s asymmetric transfer hydrogenation while the Z-trisubstituted double bond was formed by a regioselective hydrostannation of an alkyne followed by methylation of the resultant vinyl stannane using Lipshutz’s protocol. The C18 chiral centre was introduced by a chemoenzymatic route.”

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