AI Article Synopsis
- The study presents the first asymmetric total synthesis of apratoxin D, a powerful compound that inhibits human lung cancer cell growth with an IC(50) value of 2.6 nM.
- To achieve this, the researchers used asymmetric N-amino cyclic carbamate α,α-bisalkylation to effectively create the C-37 methyl group with high selectivity.
- Additionally, they implemented key asymmetric reactions, including Evans syn-aldol and Paterson anti-aldol transformations, both demonstrating excellent stereoselectivity.
Article Abstract
The first asymmetric total synthesis of the marine natural product apratoxin D, a highly potent inhibitor of H-460 human lung cancer cell growth (IC(50) value of 2.6 nM), is described. Asymmetric N-amino cyclic carbamate (ACC) α,α-bisalkylation was utilized to establish the isolated C-37 methyl group with excellent selectivity. Other key asymmetric transformations employed were an Evans syn-aldol and a Paterson anti-aldol, both of which also proceeded with excellent stereoselectivity.
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| http://dx.doi.org/10.1021/ol302309c | DOI Listing |
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