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

doi:10.3390/molecules28010300

Molecules (Dec 2022)

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

DOI: https://doi.org/10.3390/molecules28010300
Journal volume & issue: Vol. 28, no. 1
p. 300

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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