Langille Neil F, Panek James S
Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Org Lett. 2004 Sep 2;6(18):3203-6. doi: 10.1021/ol048664r.
[reaction: see text] A convergent enantioselective synthesis of the natural product (-)-callystatin A (1) is described. Key features of the synthesis include a lipase-mediated kinetic resolution to install the C5 lactone stereochemistry, a hydrozirconation-based approach to the C8-C9 trisubstituted (Z)-olefin, and a stereoselective cross-coupling of a vinyl dibromide to install the C14-C15 trisubstituted (E)-olefin.
[反应:见正文] 本文描述了天然产物(-)-加利他汀A(1)的对映选择性汇聚合成。该合成的关键特征包括通过脂肪酶介导的动力学拆分来构建C5内酯的立体化学,采用基于锆氢化反应的方法构建C8-C9三取代(Z)-烯烃,以及通过乙烯基二溴化物的立体选择性交叉偶联来构建C14-C15三取代(E)-烯烃。