Highly Efficient and Mild Gold (I) Catalyzed Synthesis of 3,8-Diarylidene-2,7-dioxaspiro[4.4]nonane-1,6-diones
Antonia Iazzetti,
Dario Allevi,
Andrea Calcaterra,
Giancarlo Fabrizi,
Antonella Goggiamani,
Giulia Mazzoccanti,
Alessio Sferrazza,
Rosanna Verdiglione,
Valeria Vergine
Affiliations
Antonia Iazzetti
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
Dario Allevi
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
Andrea Calcaterra
Department of Chemistry and Technology of Drugs, Sapienza-University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy
Giancarlo Fabrizi
Department of Chemistry and Technology of Drugs, Sapienza-University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy
Antonella Goggiamani
Department of Chemistry and Technology of Drugs, Sapienza-University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy
Giulia Mazzoccanti
Department of Chemistry and Technology of Drugs, Sapienza-University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy
Alessio Sferrazza
Department of Chemistry and Technology of Drugs, Sapienza-University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy
Rosanna Verdiglione
Department of Chemistry and Technology of Drugs, Sapienza-University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy
Valeria Vergine
Department of Chemistry and Technology of Drugs, Sapienza-University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy
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.
