Synthesis 2006(21): 3605-3610  
DOI: 10.1055/s-2006-950215
PAPER
© 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
Fax: +1(510)6429675; e-Mail: rsarpong@berkeley.edu;
Further Information

Publication History

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

Abstract

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.

    References

  • 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 
8

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