Download PDF
Synthesis 2009(3): 379-384  
DOI: 10.1055/s-0028-1083303
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Intramolecular Ketalization of Functionalized 7-Norbornenols

Leo A. Paquette*, Jeremy D. Pettigrew
Evans Chemical Laboratories, The Ohio State University, 100 West 18th Avenue, Columbus, OH 43210, USA
Fax: +1(614)2921685; e-Mail: paquette.1@osu.edu;
Further Information

Publication History

Received 6 August 2008
Publication Date:
09 January 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

Convenient access to polycondensed heterocyclic networks has been realized through exposure of bridged hydroxy acetonides to appropriate reagents.

Key words - photochemistry - heterocycles - acetals - sulfones - sulfoxides

    References

  • For reports on efforts towards the synthesis of pseudolaric acid A(1), see:
  • 1a Geng Z. Chen B. Chiu P. Angew. Chem. Int. Ed.  2006,  45:  6197 
    Google Scholar
  • 1b Chen B. Ko RYY. Yuen MSM. Cheng KF. Chiou P. J. Org. Chem.  2003,  68:  495 
    Google Scholar
  • 1c Chiu P. Chen B. Cheng KF. Org. Lett.  2001,  3:  1721 
    Google Scholar
  • 1d Ou L. Hu Y. Song G. Bai D. Tetrahedron  1999,  55:  13999 
    Google Scholar
  • 1e Hu Y. Ou L. Bai D. Tetrahedron Lett.  1999,  40:  545 
    Google Scholar
  • 1f Chiu P. Chen B. Cheng KF. Tetrahedron Lett.  1998,  39:  9229 
    Google Scholar
  • 1g Pan BC. Chang HY. Cai GL. Guo YS. Pure Appl. Chem.  1989,  61:  389 
    Google Scholar
  • 2a Zhou BN. Ying BP. Song GQ. Chen ZX. Han J. Yan YF. Planta Med.  1983,  47:  35 
    Google Scholar
  • 2b Yao JX. Lin XY. Acta Chim. Sin. (Engl. Ed.)  1982,  40:  385 
    Google Scholar
  • 3a Cargill RL. Peet NP. Pond DM. Bundy WA. Sears AB. J. Org. Chem.  1980,  45:  3999 
    Google Scholar
  • 3b Cargill RL. Sears AB. Boehm J. Willcott MR. J. Am. Chem. Soc.  1973,  95:  4346 
    Google Scholar
  • 3c Cargill RL. King TY. Sears AB. J. Org. Chem.  1971,  36:  1423 
    Google Scholar
  • 3d Cargill RL. Sears AB. Willcott MR. J. Am. Chem. Soc.  1970,  92:  6084 
    Google Scholar
  • 3e Cargill RL. Gimare BM. Pond DM. King TY. Sears AB. Willcott MR. J. Am. Chem. Soc.  1970,  92:  3809 
    Google Scholar
  • 4 Basil LF. Nakano H. Frutos R. Kopach M. Meyers AI. Synthesis  2002,  2064 
    Article in Thieme ConnectGoogle Scholar
  • 5 Snider BB. Allentoff AJ. Kulkarni YS. J. Org. Chem.  1988,  53:  5320 
    CrossrefGoogle Scholar
  • 6a Langer K. Mattay J. J. Org. Chem.  1995,  60:  7256 
    Google Scholar
  • 6b Salomon RG. Coughlin DJ. Ghosh S. Zagorski MG. J. Am. Chem. Soc.  1982,  104:  998 
    Google Scholar
  • 7 More JD. Finney NS. Org. Lett.  2002,  4:  3001 
    CrossrefGoogle Scholar
  • 8 Nicolaou KC. Montagnon T. Baran PS. Angew. Chem. Int. Ed.  2002,  41:  1386 
    CrossrefGoogle Scholar
  • 9 The use of catalytic Pd(OAc)2 resulted in lower yields. See: Larock RC. Hightower TR. Kraus GA. Hahn P. Zheng D. Tetrahedron Lett.  1995,  36:  2423 
    CrossrefGoogle Scholar
  • 10 Rigby JH. Wilson JAZ. J. Org. Chem.  1987,  52:  34 
    CrossrefGoogle Scholar
  • 11 This material was found to contain a small amount of the corresponding syn-alcohol (10:1 anti/syn). The assignment of the relative stereochemistry at the newly formed stereogenic center was made on the basis of the ¹H NMR chemical shifts of the signals corresponding to the vinyl and bridgehead protons (anti δ = 5.29/syn δ = 5.55 and anti δ = 2.29/syn δ = 2.38, respectively). See: Clark FRS. Warkentin J. Can. J. Chem.  1971,  49:  2223 
    CrossrefGoogle Scholar
  • For examples of the McMurry reaction used to for polycycles containing seven-membered rings, see
  • 12a Dauben WG. Farkas I. Bridon DP. Chuang CP. Henegar KE. J. Am. Chem. Soc.  1991,  113:  5883 
    Google Scholar
  • 12b Lee E. Yoon CH. Tetrahedron Lett.  1996,  37:  5929 
    Google Scholar
  • 13a Roberts JD. Johnson FO. Carboni RA. J. Am. Chem. Soc.  1954,  76:  5692 
    Google Scholar
  • 13b Winstein S. Shatavsky M. Norton C. Woodward RB. J. Am. Chem. Soc.  1955,  77:  4183 
    Google Scholar
  • 14 For examples of α-sulfonyl sulfones being used in Ramberg-Bäcklund ring contraction reactions, see: Scarpetti D. Fuchs PL. J. Am. Chem. Soc.  1990,  112:  8084 
    CrossrefGoogle Scholar
  • 15 Armarego WLF. Perrin DD. Purification of Laboratory Chemicals   4th ed.:  Butterworth-Heinemann; Oxford: 1997. 
    Google Scholar
  • 16 Still WC. Kahn M. Mitra A. J. Org. Chem.  1978,  43:  2923 
    CrossrefGoogle Scholar
17

Signal disappeared upon the addition of a drop of D2O to the NMR sample.