Perepogu Arun Kumar, Raman D, Murty U S N, Rao Vaidya Jayathirtha
Organic Chemistry Division-II, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500 607, Andhra Pradesh, India.
Bioorg Chem. 2009 Apr;37(2):46-51. doi: 10.1016/j.bioorg.2008.12.002. Epub 2009 Jan 21.
The first total synthesis of 9-membered macrolide, stagonolide-F (3), starting from commercially available 1,5-pentane diol is reported. A combination of Jacobsen's hydrolytic kinetic resolution (HKR) and Sharpless epoxidation is used for the creation of two stereogenic centers, while ring-closing metathesis (RCM) strategy was used for the construction of the lactone ring. The molecule synthesized exhibited potent antifungal, antibacterial and cytotoxic activities against all the tested strains.
报道了从市售的1,5 - 戊二醇出发首次全合成9元大环内酯类化合物——链格孢菌素 - F（3）。采用雅各布森水解动力学拆分（HKR）和夏普莱斯环氧化反应相结合的方法构建了两个手性中心，同时采用关环复分解（RCM）策略构建内酯环。合成的分子对所有测试菌株均表现出强效的抗真菌、抗菌和细胞毒性活性。
