Kuang Ze, Ding Xiao-Bo, Li Freda F, Brimble Margaret A
School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland 1010, New Zealand.
The Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3 Symonds Street, Auckland 1010, New Zealand.
ACS Omega. 2024 Oct 31;9(45):45624-45632. doi: 10.1021/acsomega.4c08699. eCollection 2024 Nov 12.
The synthesis of the spirocyclic imine fragment of the portimine family of marine toxins has been achieved. A densely functionalized key lactone-ester intermediate was assembled via a highly diastereoselective Diels-Alder cycloaddition, involving a novel γ-hydroxymethyl-α,β-butenolide dienophile. A Stille coupling was employed to install the vinyl group. Selective elaboration of the two carbonyl groups successfully afforded the spirocyclic imine fragment.
海洋毒素波替米星家族的螺环亚胺片段已成功合成。通过高度非对映选择性的狄尔斯-阿尔德环加成反应，构建了一个官能团密集的关键内酯-酯中间体，该反应涉及一种新型的γ-羟甲基-α,β-丁烯内酯亲双烯体。采用施蒂勒偶联反应引入乙烯基。对两个羰基进行选择性修饰，成功得到了螺环亚胺片段。
