Friday, January 20, 2017

Uses for Akanocure Stereotetrad Lactones 3: lactone openings with secondary 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. These lactones can be ring-opened using secondary nitrogens as the nucleophilic agent. Previously, this reaction has been used to synthesize portions of Aplyronine A, a potent, chemotherapeutic marine macrolide. This research holds promise for enhanced synthesis of difficult-to-source chemotherapy agents. Read more: Hong, Wan Pyo, Mohammad N. Noshi, Ahmad El-Awa, and Philip L. Fuchs. "Synthesis of the C1–C20 and C15–C27 Segments of Aplyronine A." Organic letters 13, no. 24 (2011): 6342-6345. http://pubs.acs.org/doi/abs/10.1021/ol2024746

“Abstract: The synthesis of C1–C20 and C15–C27 segments of Aplyronine A is described. Oxidative cleavage of cyclic vinyl sulfones has been used to prepare key fragments of Aplyronine A. Key precursors are united by Horner–Wadsworth–Emmons and Julia–Kociensky olefination for the respective elaboration of the C1–C20 and C15–C27 segments.”
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