Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
Org Lett. 2010 Mar 5;12(5):988-91. doi: 10.1021/ol902984e.
The synthesis of a C1-C19 precursor to pectenotoxin 4 is presented. The strategy employed the functionalized allene shown. Key features include: olefin metathesis of two simple fragments to prepare the left portion of the allene-precursor, diastereoselective propargylation of an epoxy aldehyde to form the right portion, use of the DMDO-stable m-fluorobenzyl ether, and an allene spirodiepoxidation/C-ring formation cascade.
本文介绍了扇贝毒素 4 的 C1-C19 前体的合成。所采用的策略包括所示的功能化丙二烯。关键特征包括:通过两个简单片段的烯烃复分解反应制备丙二烯前体的左侧部分,对环氧醛进行非对映选择性炔丙基化反应形成右侧部分,使用 DMDO 稳定的间氟苄基醚,以及丙二烯螺环二环氧/ C 环形成级联反应。