从碳水化合物衍生的末端未取代二烯和芳基炔烃中立体选择性合成 1,2-稠合-C-芳基糖苷：在糖稠合或支化萘和 C-芳基糖苷合成中的应用。
Stereoselective synthesis of 1,2-annulated-C-Aryl glycosides from carbohydrate-derived terminally unsubstituted dienes and arynes: Application towards synthesis of sugar-fused- or branched- naphthalenes, and C-Aryl glycosides.
机构信息
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.
出版信息
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。
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