American Chemical Society
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Stereoselective Synthesis of (±)-Cephanolide B

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journal contribution
posted on 2021-11-16, 14:05 authored by Anding Li, Ziru He, Bingyan Liu, Zhen Yang, Zichun Zhang
A concise and stereoselective total synthesis of (±)-cephanolide B was achieved in 15 steps. The key steps in the synthesis were as follows: (i) an intermolecular Diels–Alder reaction followed by lactonization to form the oxabicyclo[2.2.2]­octane DE ring; (ii) a tandem reaction, featuring an intramolecular Pauson–Khand reaction, a 6π-electrocyclization, and an oxidative aromatization by O2, to construct the ABC-tricyclic rings (6-5-6); and (iii) a phthaloyl peroxide-mediated arene oxygenation to install the C-13 phenol group.