Synlett 2008(14): 2087-2088  
DOI: 10.1055/s-2008-1078569
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Studies towards the Synthesis of Coprinolone, Δ6-Coprinolone, and Radulone A via an Anionic Electrocyclization Cascade

Andrew L. Lawrence, Victor Lee*, Robert M. Adlington*
Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK
Fax: +44(1865)275632; e-Mail: robert.adlington@chem.ox.ac.uk; e-Mail: victor.lee@chem.ox.ac.uk;
Further Information

Publication History

Received 9 May 2008
Publication Date:
15 July 2008 (online)

Abstract

Studies towards the synthesis of coprinolone, Δ6-coprinolone, and radulone A, resulting in the synthesis of an advanced intermediate with the tricyclic protoilludane carbon skeleton, are described.

    References and Notes

  • 1a Starrat AN. Ward EWB. Stothers JB. Can. J. Chem.  1989,  67:  417 
  • 1b Starrat AN. Ward EWB. Stothers JB. J. Chem. Soc., Chem. Commun.  1988,  9:  590 
  • 2 Fabian K. Lorenzen K. Anke T. Johansson M. Sterner O. Z. Naturforsch., C: Biosci.  1998,  53:  939 
  • 3 Abraham WR. Curr. Med. Chem.  2001,  8:  583 
  • 4 Lawrence AL. Wegner HA. Jacobsen MF. Adlington RM. Baldwin JE. Tetrahedron Lett.  2006,  47:  8717 
  • 5 Travis BR. Narayan RS. Borhan B. J. Am. Chem. Soc.  2001,  124:  3824 
  • 6a Peelen TJ. Chi Y. English EP. Gellman SH. Org. Lett.  2004,  6:  4411 
  • 6b

    It should be noted that addition of the diester to the basic solution had to be slow (³ 4 h) otherwise low yields of impure product were obtained.

  • 7a Comins DL. Dehghani A. Tetrahedron Lett.  1992,  42:  6299 
  • 7b Comins DL. Dehghani A. Foti CJ. Joseph SP. Org. Synth.  1997,  74:  77 
  • 8 General procedure for Pd-catalyzed Negishi coupling taken from: Milne JE. Buchwald SL. J. Am. Chem. Soc.  2004,  126:  13028 
  • 9 Luche JL. Petrier C. Einhorn J. Tetrahedron Lett.  1985,  26:  1445 
  • 10 Frigerio M. Santagostino M. Tetrahedron Lett.  1994,  35:  8019 
  • 11 Snider BB. Harvey TC. J. Org. Chem.  1994,  59:  504