1204751-50-7Relevant academic research and scientific papers
The Evolution of the Total Synthesis of Rocaglamide
Zhou, Zhe,Dixon, Darryl D.,Jolit, Anais,Tius, Marcus A.
, p. 15929 - 15936 (2016)
The complex flavagline, (?)-rocaglamide, possesses a synthetically intriguing tricyclic scaffold with five contiguous stereocenters and also exhibits potent anticancer, anti-inflammatory and insecticidal activity. This full account details distinct approaches to (±)- and (?)-rocaglamide utilizing Br?nsted acid catalyzed and asymmetric Pd0-catalyzed Nazarov chemistry developed in our laboratory, respectively. The successful asymmetric synthesis revealed unforeseen mechanistic complexity that required adjusting our strategy to overcome an unanticipated racemization process, an unusual reversible ring-cleavage step and a very facile trialkylsilyl group migration.
Enamine-lminium ion nazarov cyclization of α-ketoenones
Bow, William F.,Basak, Ashok K.,Jolit, Anais,Vicic, David A.,Tius, Marcus A.
supporting information; experimental part, p. 440 - 443 (2010/04/24)
[Chemical equaction presented] The mono-triflate salts of some chiral nonracemic 1,2-diamines react with α-ketoenones in a stoichiometric reaction to form products of the Nazarov cyclization in high enantiomeric ratios. The mechanism appears to involve rearrangement of an enamine-iminium ion.
