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SYNTHESIS OF THE BICYCLO[3.3.1]NONANE CORE OF HUPERZINE A AND NOVEL PYRIDINE-FUSED TRICYCLES BY CYCLISATION OF PYRIDINE-BASED RADICALS

  作者 WARD JARROD; CAPRIO VITTORIO  
  选自 期刊  Heterocycles;  卷期  2009年79-1;  页码  791-804  
  关联知识点  
 

[摘要]The cyclisation of 3-pyridyl radicals and (2-pyridyl)methyl radicals, generated from (pyridyl)cyclohexenols 5 to 8, has been examined as part of a model study directed towards the synthesis of huperzine A. The 3-pyridyl radical, generated from 3-bromopyridine 5, undergoes 5-exo-trig cyclisation to give hexahydroindenopyridine 10. Related pyridine-fused tricycle 12 is formed by 5-exo-trig cyclization of the (2-pyridyl)methyl radical derived from selenide 7b, while the radicals generated from selenides 8b and 19 undergo 6-exo-trig cyclisation to give the bicyclo[3.3.1]nonane core of huperzine A.

 
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