Université Paris-Saclay Lipides;
Université Paris-Saclay;
Synthèse (BioCIS);
Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO);
systèmes analytiques et biologiques [lip(sys)2;
CNRS Biomolécules;
Conception;
Isolement;
CNRS;
关键词：
xerocomic acid;
fluorescence;
pulvinic acids;
total synthesis;
Suzuki Miyaura;
期刊名称：
European journal of organic chemistry
i s s n：
1434-193X
年卷期：
2023 年
26 卷
8 期
页 码：
n/a-n/a
页 码：
摘 要：
Abstract A set of representative pulvinic acids were synthesised using a bioinspired strategy. Terphenyl‐quinones (polyporic acid scaffold) were prepared via sequential Suzuki‐Miyaura couplings allowing access to unsymmetrically substituted derivatives in a one‐pot protocol. Subjected to the action of acetic anhydride and DMSO, quinones were converted into bis‐lactone intermediates. Methanolysis and deprotection achieved the total syntheses of the corresponding pulvinic acids. Following this general strategy, symmetrical pulvinic, atromentic, variegatic acids and unsymmetrical congener pinastric, iso‐pinastric, xerocomic and iso‐xerocomic acids were prepared in fair yields. Fluorescence properties were observed for the bis‐lactone intermediates and, as a complement to this synthetic work, optical properties were measured, and fluorescence quantum yields were determined for the bis‐lactone pigments.
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