CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
J Org Chem. 2012 Nov 2;77(21):9840-5. doi: 10.1021/jo301425c. Epub 2012 Oct 15.
This paper describes the formal total synthesis of (+)-neopeltolide, a cytotoxic macrolide isolated from the marine sponge Neopeltidae. The key features of the synthesis include an asymmetric Evans alkylation to fix the C9-methyl center, Jacobsen hydrolytic kinetic resolution of terminal epoxides followed by their regioselective opening to fix the stereocenters at the C11 and C13 positions, respectively, a Pd-catalyzed oxa-Michael reaction to construct the tetrahydropyran ring, and Yamaguchi macrolactonization to form the macrocyclic core of the molecule.
本文描述了 (+)-新仙霉素的全合成，新仙霉素是一种从海洋海绵 Neopeltidae 中分离得到的细胞毒性大环内酯。该合成的关键特点包括：不对称 Evans 烷基化反应来固定 C9-甲基中心；Jacobsen 水解动力学拆分末端环氧化物，然后区域选择性开环，分别固定 C11 和 C13 位置的立体中心；钯催化的氧杂-Michael 反应构建四氢吡喃环；以及 Yamaguchi 大环内酯化形成分子的大环核心。
