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Concise Total Synthesis of (+/-)-Cephalotaxine via a Transannulation Strategy: Development of a Facile Reductive oxy-Nazarov Cyclization

  作者 LI WEIDONG Z; DUO WEIGUO; ZHUANG CHENGHAN  
  选自 期刊  Organic Letters;  卷期  2011年13-13;  页码  3538-3541  
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[摘要]A concise total synthesis of (+/-)-cephalotaxine (1) has been achieved from dioxolanone derivative 15 via a transannulation strategy. The key transformation is a facile reductive oxy-Nazarov cyclization as illustrated above, involving presumably a tethered 1,2-oxidopentadienyl cation species 7a or 7b, which represents a new variant of the oxy-Nazarov cyclization and constitutes an effective, regio- and stereospeclfic 5-hydroxy cyclopentenone annulation protocol under mild hydride reduction conditions.

 
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