| Autor: |
Liu J; School of Pharmacy and Food Engineering, Wuyi University, Jiangmen, 529020, China.; State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, University Town, Xili, Shenzhen, 518055, China., Chen K; State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, University Town, Xili, Shenzhen, 518055, China., Guo Y; State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, University Town, Xili, Shenzhen, 518055, China., Chen Y; State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, University Town, Xili, Shenzhen, 518055, China., Ye T; State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, University Town, Xili, Shenzhen, 518055, China.; Qian Yan (Shenzhen) Pharmatech. Ltd., Shenzhen 518172, China. |
| Abstrakt: |
Actin stabilizers that are capable of interfering with actin cytoskeleton dynamics play an important role in chemical biology. Rhizopodin, a novel actin stabilizer, affects the actin cytoskeleton at nanomolar concentrations and exhibits potent antiproliferative activities against a range of tumor cell lines with IC 50 values in the low nanomolar range. Herein, we report the total synthesis of rhizopodin based on a late-stage oxazole ring formation strategy, whose success demonstrates the feasibility of late-stage oxazole ring formation in the synthesis of complex oxazole containing natural products. Other features of the synthesis include a Nagao aldol reaction, a Suzuki coupling, a Yamaguchi esterification, a modified Robinson-Gabriel synthesis of the oxazoles, and a bidirectional Ba(OH) 2 -mediated Horner-Wadsworth-Emmons (HWE) reaction. |
