Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Tokyo 108-8641, Japan.
J Am Chem Soc. 2013 Aug 28;135(34):12568-71. doi: 10.1021/ja406657v. Epub 2013 Aug 19.
A first asymmetric total synthesis and determination of the absolute configuration of neoxaline has been accomplished through the highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (-)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline as the key steps.
首次通过高度立体选择性地引入反式prenyl 基团，使用 (-)-3a-羟基呋喃并吲哚啉作为构建块，构建吲哚啉螺环亚胺通过逐步氧化和环化从吲哚啉开始，组装（Z）-脱氢组氨酸，以及非天然（Z）-新诺林的光异构化为关键步骤，完成了新诺林的首次不对称全合成和绝对构型的确定。
