56245-51-3Relevant articles and documents
Five-Step Total Synthesis of (±)-Aspidospermidine by a Lactam Strategy via an Azomethine Ylide
Katahara, Seiya,Sugiyama, Yasukazu,Yamane, Mina,Komiya, Yukinori,Sato, Takaaki,Chida, Noritaka
, p. 3058 - 3063 (2021/05/04)
A five-step total synthesis of (±)-aspidospermidine (1) based on a lactam strategy is reported. Our synthesis features an iridium-catalyzed reductive Michael addition/[3+2] cycloaddition cascade to give a tricyclic ketone intermediate from a simple lactam via an azomethine ylide. The developed strategy enables easily available lactams to be used as stable surrogates of multisubstituted amines and would be applicable to a unified total synthesis of complex Aspidosperma alkaloids.
Asymmetric Total Synthesis of (+)-Winchinine B
Liu, Zaimin,Ju, Xiaolin,Ma, Shiqiang,Du, Chenglong,Zhang, Weiwei,Li, Huilin,Wang, Xiaolei,Xie, Xingang,She, Xuegong
, p. 14994 - 15000 (2019/11/19)
The first asymmetric total synthesis of aspidosperma alkaloid (+)-winchinine B was achieved in 12 steps from commercially available materials. A new synthetic strategy which features an efficient aza-Michael addition, a ruthenium-catalyzed transfer dehydrogenation, and an intramolecular palladium-catalyzed oxidative coupling was adopted to install the ABC tricycle system. A one-pot process involving carbonyl reduction/iminium formation/intramolecular conjugate addition developed by our group was utilized to construct the D ring moiety.
Enantioselective Synthesis of (-)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation
Antropow, Alyssa H.,Garcia, Nicholas R.,White, Kolby L.,Movassaghi, Mohammad
supporting information, p. 3647 - 3650 (2018/06/26)
The first enantioselective total synthesis of (-)-vallesine via a strategy that features a late-stage regioselective C17-oxidation followed by a highly stereoselective transannular cyclization is reported. The versatility of this approach is highlighted by the divergent synthesis of the archetypal alkaloid of this family, (+)-aspidospermidine, and an A-ring-oxygenated derivative, (+)-deacetylaspidospermine, the precursor to (-)-vallesine, from a common intermediate.
