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• W3203481388 abstract "Tomatidine has recently generated a lot of interest amongst the pharmacology, medicine, and biology fields of study, especially for its newfound activity as an antibiotic agent capable of targeting multiple strains of bacteria. In the light of its low natural abundance and high cost, an efficient and scalable multi-gram synthesis of tomatidine has been developed. This synthesis uses a Suzuki-Miyaura-type coupling reaction as a key step to graft an enantiopure F-ring side chain to the steroidal scaffold of the natural product, which was accessible from low-cost and commercially available diosgenin. A Lewis acid-mediated spiroketal opening followed by an azide substitution and reduction sequence is employed to generate the spiroaminoketal motif of the natural product. Overall, this synthesis produced 5.2 g in a single pass in 15 total steps and 15.2% yield using a methodology that is atom economical, scalable, and requires no flash chromatography purifications." @default.
• W3203481388 created "2021-10-11" @default.
• W3203481388 creator A5041729989 @default.
• W3203481388 creator A5078046666 @default.
• W3203481388 date "2021-10-03" @default.
• W3203481388 modified "2023-10-02" @default.
• W3203481388 title "Concise Large-Scale Synthesis of Tomatidine, A Potent Antibiotic Natural Product" @default.
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• W3203481388 doi "https://doi.org/10.3390/molecules26196008" @default.
• W3203481388 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/8512692" @default.
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