Department of Chemistry, Indiana University, Bloomington, Indiana 47405, United States.
Org Lett. 2020 Jun 5;22(11):4118-4122. doi: 10.1021/acs.orglett.0c01177. Epub 2020 May 8.
A stereocontrolled synthesis of , the C(10)-C(25) component of amphidinolide C (), has been efficiently achieved. Reaction of the dithiane component with nonracemic bis(epoxide) directly affords functionalized 2,5--disubstituted tetrahydrofuran . Propargylation is highly diastereoselective for the formation of the desired C(12)-C(13) stereochemistry, and the resulting terminal alkyne is utilized for a regioselective -silylstannylation. A general strategy is illustrated for sequential replacement of stannyl and silyl substituents of the trisubstituted alkene to yield ()-alkenyl iodide .
一种立体控制的合成方法，用于合成 Amphidinolide C () 的 C(10)-C(25) 部分，已经被有效地实现了。二硫戊环组件 与非手性双环氧化物 直接反应，直接提供功能化的 2,5--二取代四氢呋喃 。炔丙基化对于形成所需的 C(12)-C(13) 立体化学具有高度的非对映选择性，并且得到的末端炔烃 被用于区域选择性的 -硅基锡化。说明了一种用于连续取代三取代烯烃的锡基和硅基取代基的一般策略，以生成 ()-烯基碘化物 。
