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An efficient and tunable route to AG7088, a rhinovirus protease inhibitor
Dawei Ma1, Weiqing Xie1, Bin Zou1
1State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Tetrahedron Letters
|April 15, 2020
Abstract:
Aldol reaction of N,N-dibenzyl valinal with propiolic acid ethyl ester derived lithium reagent provides anti-aminoalcohol 8 and syn-aminoalcohol 9, which are converted into the lactone 6 via two different routes. Alkylation of 6 followed by lactone ring opening afford the acid 2a, which is coupled with the amine 3 and 5-methylisoxazole-3-carboxylate acid 1, respectively, to deliver AG7088.
