55281-55-5Relevant academic research and scientific papers
Eight-Step Enantioselective Total Synthesis of (?)-Cycloclavine
McCabe, Stephanie R.,Wipf, Peter
, p. 324 - 327 (2017)
The first enantioselective total synthesis of (?)-cycloclavine was accomplished in 8 steps and 7.1 % overall yield. Key features include the first catalytic asymmetric cyclopropanation of allene, mediated by the dirhodium catalyst Rh2(S-TBPTTL)4, and the enone 1,2-addition of a new TEMPO carbamate methyl carbanion. An intramolecular strain-promoted Diels–Alder methylenecyclopropane (IMDAMC) reaction provided a pivotal tricyclic enone intermediate with more than 99 % ee after crystallization. The synthesis of (?)-1 was completed by a late-stage intramolecular Diels–Alder furan (IMDAF) cycloaddition to install the indole.
