Highly Efficient and Mild Gold (I) Catalyzed Synthesis of 3,8-Diarylidene-2,7-dioxaspiro[4.4]nonane-1,6-diones |
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| Authors: | Antonia Iazzetti Dario Allevi Andrea Calcaterra Giancarlo Fabrizi Antonella Goggiamani Giulia Mazzoccanti Alessio Sferrazza Rosanna Verdiglione Valeria Vergine |
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| Affiliation: | 1.Dipartimento di Scienze Biotecnologiche di Base Cliniche Intensivologiche e Perioperatorie, Università Cattolica del Sacro Cuore, Campus di Roma, Largo Francesco Vito 1, 00168 Rome, Italy;2.Department of Chemistry and Technology of Drugs, Sapienza-University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy |
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| Abstract: | The gold-catalyzed cyclization of 2,2-bis(3-arylprop-2-yn1-yl)malonic acid has been proposed as an efficient approach to substituted 3,8-dibenzyl-2,7-dioxaspiro[4.4]nonane-1,6-diones. The reaction proceeds smoothly in mild reaction conditions to give the desired products in quantitative yields in the presence of variously substituted starting materials. In addition, the synthesis of γ-arylidene spirobislactone bearing different substituents on the two aromatic rings has been achieved. This kind of compound could be of great interest in pharmaceutical science given the widespread presence of this scaffold in bioactive natural and synthetic products. |
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| Keywords: | spirobislactone spirolactone spiro compounds Au(I)-catalyzed cyclization alkyne activation heterocyclization |
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