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Synlett 1996; 1996(7): 625-627
DOI: 10.1055/s-1996-5557
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A Facile Oxy-Cope Rearrangement Route to Functionalized Bicyclo[5.3.1]undecane Ring System Present in Taxol and Vinigrol Diterpenoids

Goverdhan Mehta* , K. Subba Reddy
  • *Molecular Design and Synthesis Unit of JNCASR, School of Chemistry, University of Hyderabad, Hyderabad, 500 046, India
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Publication Date:
31 December 2000 (online)

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An oxy-Cope rearrangement based protocol to bicyclo[5.3.1]undecane ring system from a readily and abundantly available bicyclo[4.4.0]decane precursor is described. Several interesting transformations leading to the formation of tricyclo[6.2.1.04,11]undecane system among others are also reported.

Taxol and vinigrol diterpenoids - [3,3]sigmatropic rearrangement - carbonyl-enereaction - carbonyl-olefin transannular cyclization - functional group switching

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