Ganaie Bilal Ahmad, Balasubramani Alagesan, Bhat Bilal A, Mehta Goverdhan
School of Chemistry, University of Hyderabad, Hyderabad 500046, India.
Natural Products & Medicinal Chemistry, CSIR-Indian Institute and Integrative Medicine Sanatnagar, Srinagar 190005, India.
J Org Chem. 2023 Aug 18;88(16):11637-11649. doi: 10.1021/acs.joc.3c00958. Epub 2023 Aug 9.
A mild, scalable, one-pot access to multifunctional 9-fluorenols from -formyl-ynones and -bis-ynones on reaction with dimethylacetone-1,3-dicarboxyate through tandem Michael addition-Aldol condensation cascade has been conceptualized and executed. The scope and utility of this synthetic approach have been further amplified for one-pot entry into functionally enhanced, higher order fluorenols like pentacyclic indeno[1,2-]fluorene-6,12-diols and further to indeno[1,2-]fluorene-6,12-diones through the implementation of "double indeno-annulation" tactic on -bis--formyl ynones and dimethylacetone-1,3-dicarboxylate. Besides several green attributes, the current approach is also compatible with the emerging time and energy economy features and is a swift gateway to build complexity.
通过串联迈克尔加成-羟醛缩合级联反应，从α-甲酰基炔酮和α,α'-双炔酮与丙酮-1,3-二羧酸二甲酯反应，温和、可扩展、一锅法制备多功能9-芴醇的方法已被构思并实施。通过对α,α'-双-α-甲酰基炔酮和丙酮-1,3-二羧酸二甲酯实施“双茚并环化”策略，这种合成方法的范围和实用性得到进一步扩展，可一锅法制备功能增强的高阶芴醇，如五环茚并[1,2-b]芴-6,12-二醇，并进一步制备茚并[1,2-b]芴-6,12-二酮。除了具有若干绿色特性外，当前方法还符合新兴的时间和能源经济特点，是构建复杂化合物的快速途径。
