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Asymmetric Total Synthesis of 5,10-seco-Neoansamycin A
Huacheng Xu1,2, Cheng Zou2, Adila Nazli2
1School of Science and Engineering, Shenzhen Key Laboratory of Innovative Drug Synthesis, The Chinese University of Hong Kong, Shenzhen, Shenzhen 518172, P. R. China.
None:
The first asymmetric total synthesis of 5,10-seco-neoansamycin A, a 19-membered cyclic octaketide, was achieved in 20 steps (with several steps being telescoped) and 6.7% overall yield starting from the reported compound, thus leading to the assignment of its absolute configuration. This convergent synthetic approach features late-stage macrolactamization, a judicious application of an asymmetric aldol reaction. This work will facilitate the synthesis of other ansamycin natural products and the explorations of 5,10-seco-neoansamycin A as a potential anticancer lead.
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