Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.
Carbohydr Res. 2018 Jul 30;465:29-34. doi: 10.1016/j.carres.2018.06.001. Epub 2018 Jun 6.
Synthesis of 1,2-annulated-C-aryl glycosides has been achieved in a stereoselective manner through the Diels-Alder reaction between carbohydrate-derived terminally unsubstituted dienes and in situ generated arynes. In these reactions, formation of sugar-fused (or branched) naphthalenes was also observed and found to be temperature dependent and thus constituting one of the salient features of this work. The synthetic importance of 1,2-annulated-C-aryl glycosides has been explored by transforming them into densely oxygenated products by functionalizing the unsubstituted exo-double bond. Further, 1,2-annulated-C-aryl glycosides give rapid access to C-aryl glycosides in four steps.
通过糖衍生的末端未取代二烯和原位生成的芳炔之间的 Diels-Alder 反应，以立体选择性方式合成了 1,2-稠合-C-芳基糖苷。在这些反应中，还观察到糖稠合（或支化）萘的形成，并且发现其与温度有关，因此这是该工作的显著特征之一。通过对未取代的外向双键进行官能化，将 1,2-稠合-C-芳基糖苷转化为多氧代产物，从而探索了 1,2-稠合-C-芳基糖苷的合成重要性。此外，1,2-稠合-C-芳基糖苷可以通过四步反应快速得到 C-芳基糖苷。
