1374409-94-5Relevant academic research and scientific papers
Total syntheses of anominine and tubingensin A
Bian, Ming,Wang, Zhen,Xiong, Xiaochun,Sun, Yu,Matera, Carlo,Nicolaou,Li, Ang
supporting information; experimental part, p. 8078 - 8081 (2012/07/13)
A divergent strategy for the total syntheses of the indole terpenoid anominine (1) and its natural congener tubingensin A (2) has been developed. The common intermediate 11 bearing all of the required stereogenic centers for both natural products was first assembled by employing a Ueno-Stork radical cyclization and a Sc(OTf)3-mediated Mukaiyama aldol reaction to form the key C-C bonds in a stereocontrolled manner. The route to anominine features a radical deoxygenation followed by an efficient side-chain installation, while the path to tubingensin A exploits a CuOTf-promoted 6π-electrocyclization/ aromatization sequence to forge the central region of the pentacyclic scaffold.
