Friday, January 20, 2017

Uses for Akanocure Stereotetrad Lactones 1a: 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 synthetic route has previously been used to generate peloruside A, a non-taxoid-site microtubule-stabilizing agent which has promise for chemotherapeutic actions similar to that of paclitaxel. 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: Hoye, Thomas R., Junha Jeon, Lucas C. Kopel, Troy D. Ryba, Manomi A. Tennakoon, and Yini Wang. "Total Synthesis of Peloruside A through Kinetic Lactonization and Relay Ring‐Closing Metathesis Cyclization Reactions." Angewandte Chemie International Edition 49, no. 35 (2010): 6151-6155. http://onlinelibrary.wiley.com/doi/10.1002/anie.201002293/full

“Abstract: A convergent total synthesis of peloruside A (1) is described. The key strategic features are a diastereoselective lactonization to generate a C5–C9 valerolactone from the C2-symmetric ketone 3, and a relay ring-closing metathesis reaction to produce a dehydrovalerolactone 2. A new isomer of 1, the valerolactone isopeloruside A (iso-1), was identified. MOM=methoxymethyl.”
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