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- Title
Total Synthesis of Metaphanine and Oxoepistephamiersine.
- Authors
Sun, Ya‐Kui; Qiao, Jin‐Bao; Xin, Yu‐Meng; Zhou, Qin; Ma, Zhi‐Hua; Shao, Hui; Zhao, Yu‐Ming
- Abstract
Herein, we report a concise and divergent synthesis of the complex hasubanan alkaloids metaphanine and oxoepistephamiersine from commercially available and inexpensive cyclohexanedione monoethylene acetal. Our synthesis features a palladium‐catalyzed cascade cyclization reaction to set the tricyclic carbon framework of the desired molecules, a regioselective Baeyer–Villiger oxidation followed by a MeNH2 triggered skeletal reorganization cascade to construct the benzannulated aza[4.4.3]propellane, and a strategically late‐stage regio‐/diastereoselective oxidative annulation of sp3 C−H bond to form the challenging THF ring system and hemiketal moiety in a single step. In addition, a highly enantioselective alkylation of cyclohexanedione monoethylene acetal paved the way for the asymmetric synthesis of target molecular.
- Subjects
BAEYER-Villiger rearrangement; ASYMMETRIC synthesis; OXIDATIVE coupling; RING formation (Chemistry); CYCLOHEXANEDIONES; ALKYLATION; ANNULATION; SPIROKETALS
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 40, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202310917