1032268-47-5Relevant academic research and scientific papers
Total synthesis of (+)-lyconadin A and related compounds via oxidative C-N bond formation
West, Scott P.,Bisai, Alakesh,Lim, Andrew D.,Narayan, Raja R.,Sarpong, Richmond
supporting information; experimental part, p. 11187 - 11194 (2009/12/06)
The formation of carbon-nitrogen (C-N) bonds is a fundamental bond construction in organic synthesis and is indispensable for the synthesis of alkaloid natural products. In the context of the synthesis of the architecturally complex Lycopodium alkaloid lyconadin A, we have discovered a highly efficient oxidative C-N bond forming reaction that relies on the union of a nitrogen anion and a carbon anion. Empirical evidence amassed during our synthetic studies suggests that the mechanism of the C-N bond forming process encompasses polar as well as radical processes. Herein, we present our study of this novel C-N bond forming reaction and its application to the enantioselective total synthesis of lyconadin A and related derivatives.
Unified strategy for the synthesis of the miscellaneous Lycopodium alkaloids: Total synthesis of (±)-lyconadin A
Bisai, Alakesh,West, Scott P.,Sarpong, Richmond
, p. 7222 - 7223 (2008/12/21)
Total synthesis of the Lycopodium alkaloid lyconadin A was achieved in 18 steps starting from a readily available vinylogous ester and bromopicoline. The key step in the total synthesis is a proximity-driven oxidative C-N bond-forming reaction that yields the lyconadin pentacycle from a tetracyclic precursor. The key tetracycle, which has been prepared for the first time, is a versatile intermediate that may be utilized for the total synthesis of a variety of Lycopodium alkaloids. Critical to the success of this plan was the efficient preparation of a pyridine-annulated cycloheptadiene tricycle that promises to be a general strategy to access a variety of seven-membered ring containing natural products. Copyright
