Total Synthesis of Farnesin through an Excited-State Nazarov Reaction |
| |
| Authors: | Yonglei Que Hao Shao Dr Haibing He Prof Dr Shuanhu Gao |
| |
| Institution: | 1. Shanghai Key Laboratory of Green Chemistry and Chemical, Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062 China;2. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062 China |
| |
| Abstract: | The asymmetric total synthesis of farnesin, a rearranged ent-kaurenoid, was achieved through a convergent approach involving photo-Nazarov and intramolecular aldol cyclizations to build the syn-syn-syn hydrofluorenol ABC ring system and bicyclo3.2.1]octane CD ring system in the first application of a UV-light-induced excited-state Nazarov cyclization of a non-aromatic dicyclic divinyl ketone in a total synthesis. Unlike the conventional acid-promoted ground-state Nazarov reaction, the excited-state Nazarov reaction enables stereospecific formation of the highly strained syn-syn-syn-fused hydrofluorenone scaffold through a disrotatory cyclization. |
| |
| Keywords: | Nazarov-Cyclisierung Polycyclen Gespannte Moleküle Terpenoide Totalsynthese |
|
|
