Synthesis 2006(21): 3605-3610  
DOI: 10.1055/s-2006-950215
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Multifunctionalized Furans from Diazoallenes: Rearrangement of 6-Methylenebicyclo[3.1.0]hexanes

Tuanli Yao, Allen Hong, Richmond Sarpong*
Department of Chemistry, University of California, Berkeley, CA 94720, USA
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Further Information

Publication History

Received 30 May 2006
Publication Date:
21 August 2006 (online)


The synthesis of annulated tetrasubstituted furans using diazoallene precursors is described. This reaction provides efficient access to synthetically useful furan intermediates, which are otherwise difficult to obtain.


  • 1 Joule JA. Mills K. Heterocyclic Chemistry   4th ed., Blackwell; Oxford: 2000.  p.296 
  • 2 For an application to annulated furan synthesis, see: Zambias R. Caldwell C. Kopka I. Hammond M. J. Org. Chem.  1988,  53:  4135 
  • 3 Koenig B. In Science of Synthesis   Vol. 9:  Maas G. Thieme; Stuttgart: 2002.  p.183 
  • For recent reports from our group in this regard, see:
  • 4a Bhanu Prasad BA. Yoshimoto FK. Sarpong R. J. Am. Chem. Soc.  2005,  127:  12468 
  • 4b Pujanauski B. G., Bhanu Prasad B. A., Sarpong R.; J. Am. Chem. Soc.; 2006, 128: 6786
  • 5 For a pertinent, recent review on the trimethylmethylene-methane diyl, see: Allan AK. Carroll GL. Little RD. Eur. J. Org. Chem.  1998,  1 
  • 6 Myers AG. Zheng B. J. Am. Chem. Soc.  1996,  118:  4492 
  • 7 See, for example: Hughes CC. Kennedy-Smith JJ. Trauner D. Org. Lett.  2003,  5:  4113 

The diazoallene compounds were found to be unstable using EI techniques for mass spectrometry measurements.