160455-46-9Relevant academic research and scientific papers
Polyene cascade cyclizations mediated by BF3·CH3NO2· an unusually efficient method for the direct, stereospecific synthesis of polycyclic intermediates via cationic initiation at non-functionalized 3° alkenes. An application to the total synthesis of (±)-taxodione
Harring, Scott R.,Livinghouse, Tom
, p. 9229 - 9254 (2007/10/02)
Convenient stock solutions of BF3 gas in nitromethane have been shown to promote "H+ catalyzed" polyene cyclizations that proceed with excellent levels of regio- and stereocontrol. A direct comparison of this new method for effecting cationic polyannulations to several modern as well as classical procedures has conclusively defined the preparative advantages of the BF3·CH3NO2 medium. The utilization of these new conditions for cationic polycyclization in a concise total synthesis of the antineoplastic agent (±)-taxodione is described.
