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Synthesis 2012(3): 474-488  
DOI: 10.1055/s-0031-1289661
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereodivergent Synthesis of the C1-C9 Tetrahydropyran Subunit of Zincophorin and Isomers Thereof

François Godina,b, Ioannis Katsoulisa, Émilie Fiola-Massona, Sabrina Dhambria, Philippe Mochiriana,b, Yvan Guindon*a,b,c
a Institut de recherches cliniques de Montréal (IRCM), Bioorganic Chemistry Laboratory, 110 avenue des Pins Ouest, Montréal, QC, H2W 1R7, Canada
Fax: +1(514)9875789; e-Mail: yvan.guindon@ircm.qc.ca;
b Department of Chemistry, Université de Montréal, C.P. 6128, succursale Centre-ville, Montréal, QC, H3C 3J7, Canada
c Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montréal, QC, H3A 2K6, Canada
Further Information

Publication History

Received 13 October 2011
Publication Date:
16 January 2012 (online)

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Abstract

Zincophorin C1-C9 fragment and seven tetrahydropyran analogues were prepared diastereoselectively by sequential iodo­etherification and radical hydrogen-transfer reactions. Stereoselective formation of 3,7-trans or 3,7-cis rings was rationalized through minimization of allylic-1,3 strain in chair-like transition states. Subsequent hydrogen-transfer provided 7,8-anti or 7,8-syn isomers under acyclic stereocontrol or endocyclic control respectively. The latter approach relies on the formation of a [4.4.0] bicyclic complexes resulting from the chelation of the oxygen of the tetrahydropyran ring and the ester by a bidentate Lewis acid.

Key words

ionophore - iodoetherification - radical reduction - Lewis acid - substituted tetrahydropyrans

    References

  • 1a Song ZL. Lohse AG. Hsung RP. Nat. Prod. Rep.  2009,  26:  560 
    Search in Google Scholar
  • 1b Harrison TJ. Ho S. Leighton JL. J. Am. Chem. Soc.  2011,  133:  7308 
    Search in Google Scholar
  • 1c Mochirian P. Godin F. Katsoulis I. Fontaine I. Brazeau J.-F. Guindon Y. J. Org. Chem.  2011,  76:  7654 
    Search in Google Scholar
  • 2 Faul MM. Huff BE. Chem. Rev.  2000,  100:  2407 
    Search in Google Scholar
  • 3a Beug H. Cell  2009,  138:  623 
    Search in Google Scholar
  • 3b Gupta PB. Onder TT. Jiang GZ. Tao K. Kuperwasser C. Weinberg RA. Lander ES. Cell  2009,  138:  645 
    Search in Google Scholar
  • 4 Sippl W. In Pharmacophores and Pharmacophore Searches   Langer T. Hoffmann RD. Wiley-VCH; Weinheim: 2006.  p.395 
  • 5a Brooks HA. Gardner D. Poyser JP. King TJ.
    J. Antibiot.  1984,  37:  1501 
    Search in Google Scholar
  • 5b Gräfe U. Schade W. Roth M. Radics L. Incze M. Ujszaszy K. J. Antibiot.  1984,  37:  836 
    Search in Google Scholar
  • 7a Labelle M. Guindon Y. J. Am. Chem. Soc.  1989,  111:  2204 
    Search in Google Scholar
  • 7b Guindon Y. Yoakim C. Gorys V. Ogilvie WW. Delorme D. Renaud J. Robinson G. Lavallée JF. Slassi A. Jung G. Rancourt J. Durkin K. Liotta D.
    J. Org. Chem.  1994,  59:  1166 
    Search in Google Scholar
  • 7c Guindon Y. Slassi A. Rancourt J. Bantle G. Bencheqroun M. Murtagh L. Ghiro E. Jung G. J. Org. Chem.  1995,  60:  288 
    Search in Google Scholar
  • Selected examples involving chiral auxiliaries:
  • 8a Curran DP. Shen W. Zhang JC. Heffner TA. J. Am. Chem. Soc.  1990,  112:  6738 
    Search in Google Scholar
  • 8b Porter NA. Rosenstein IJ. Breyer RA. Bruhnke JD. Wu WX. Mcphail AT.
    J. Am. Chem. Soc.  1992,  114:  7664 
    Search in Google Scholar
  • 8c Stack JG. Curran DP. Geib SV. Rebek J. Ballester P. J. Am. Chem. Soc.  1992,  114:  7007 
    Search in Google Scholar
  • 8d Sibi MP. Ji JG. Angew. Chem., Int. Ed. Engl.  1996,  35:  190 
    Search in Google Scholar
  • 8e Sibi MP. Ji JG. J. Org. Chem.  1996,  61:  6090 
    Search in Google Scholar
  • Selected examples involving chiral Lewis acids:
  • 9a Wu JH. Radinov R. Porter NA. J. Am. Chem. Soc.  1995,  117:  11029 
    Search in Google Scholar
  • 9b Murakata M. Jono T. Mizuno Y. Hoshino O. J. Am. Chem. Soc.  1997,  119:  11713 
    Search in Google Scholar
  • 9c Porter NA. Wu JHL. Zhang GR. Reed AD. J. Org. Chem.  1997,  62:  6702 
    Search in Google Scholar
  • 10a Hart DJ. Huang HC. Krishnamurthy R. Schwartz T. J. Am. Chem. Soc.  1989,  111:  7507 
    Search in Google Scholar
  • 10b Giese B. Bulliard M. Zeitz HG. Synlett  1991,  425 
  • 10c Guindon Y. Lavallée JF. Boisvert L. Chabot C. Delorme D. Yoakim C. Hall D. Lemieux R. Simoneau B. Tetrahedron Lett.  1991,  32:  27 
    Search in Google Scholar
  • 11a Guindon Y. Faucher AM. Bourque E. Caron V. Jung G. Landry SR. J. Org. Chem.  1997,  62:  9276 
    Search in Google Scholar
  • 11b Guindon Y. Liu ZP. Jung G. J. Am. Chem. Soc.  1997,  119 :  9289 
    Search in Google Scholar
  • 11c Bouvier JP. Jung G. Liu ZP. Guérin B. Guindon Y. Org. Lett.  2001,  3:  1391 
    Search in Google Scholar
  • 12a Guindon Y. Jung G. Guérin B. Ogilvie WW. Synlett  1998,  213 
  • 12b Guindon Y. Houde K. Prévost M. Cardinal-David B. Landry SR. Daoust B. Bencheqroun M. Guérin B. J. Am. Chem. Soc.  2001,  123:  8496 
    Search in Google Scholar
  • 12c Guindon Y. Prévost M. Mochirian P. Guérin B. Org. Lett.  2002,  4:  1019 
    Search in Google Scholar
  • 12d Mochirian P. Cardinal-David B. Guérin B. Prévost M. Guindon Y. Tetrahedron Lett.  2002,  43:  7067 
    Search in Google Scholar
  • 12e Brazeau JF. Mochirian P. Prévost M. Guindon Y. J. Org. Chem.  2009,  74:  64 
    Search in Google Scholar
  • 13a Guindon Y. Lavallée JF. Llinas-Brunet M. Horner G. Rancourt J. J. Am. Chem. Soc.  1991,  113:  9701 
    Search in Google Scholar
  • 13b Guindon Y. Guérin B. Chabot C. Ogilvie W. J. Am. Chem. Soc.  1996,  118:  12528 
    Search in Google Scholar
  • 13c Guindon Y. Rancourt J. J. Org. Chem.  1998,  63:  6554 
    Search in Google Scholar
  • 14 Guérin B. Chabot C. Mackintosh N. Ogilvie WW. Guindon Y. Can. J. Chem.  2000,  78:  852 
    Search in Google Scholar
  • 15 Corey EJ. Helal CJ. Angew. Chem. Int. Ed.  1998,  37:  1987 
    Search in Google Scholar
  • 16 Bonadies F. Cardilli A. Lattanzi A. Orelli LR. Scettri A. Tetrahedron Lett.  1994,  35:  3383 
    Search in Google Scholar
  • 17a Mulzer J. Berger M. Tetrahedron Lett.  1998,  39:  803 
    Search in Google Scholar
  • 17b Haustedt LO. Panicker SB. Kleinert M. Hartung IV. Eggert U. Niess B. Hoffmann HMR. Tetrahedron  2003,  59:  6967 
    Search in Google Scholar
  • 17c Kramp GJ. Kim M. Gais HJ. Vermeeren C. J. Am. Chem. Soc.  2005,  127:  17910 
    Search in Google Scholar
  • 17d Mulzer J. Sieg A. Brucher C. Muller D. Martin HJ. Synlett  2005,  685 
  • 17e Gais HJ. Kramp GJ. Wolters D. Reddy LR. Chem. Eur. J.  2006,  12:  5610 
    Search in Google Scholar
  • 18 Sajiki H. Tetrahedron Lett.  1995,  36:  3465 
    Search in Google Scholar
  • 19a Guindon Y. Slassi A. Ghiro E. Bantle G. Jung G. Tetrahedron Lett.  1992,  33:  4257 
    Search in Google Scholar
  • 19b Guindon Y. Murtagh L. Caron V. Landry SR. Jung G. Bencheqroun M. Faucher AM. Guérin B. J. Org. Chem.  2001,  66:  5427 
    Search in Google Scholar
  • 20 Cardillo G. Orena M. Tetrahedron  1990,  46:  3321 
    Search in Google Scholar
  • 21a Bartlett PA. Meadows JD. Brown EG. Morimoto A. Jernstedt KK. J. Org. Chem.  1982,  47:  4013 
    Search in Google Scholar
  • 21b Duan JJW. Smith AB. J. Org. Chem.  1993,  58:  3703 
    Search in Google Scholar
  • 22 Laya MS. Banerjee AK. Cabrera EV. Curr. Org. Chem.  2009,  13:  720 
    Search in Google Scholar
  • 23 Tredwell M. Luft JAR. Schuler M. Tenza K. Houk KN. Gouverneur V. Angew. Chem. Int. Ed.  2008,  47:  357 
    Search in Google Scholar
  • 24a Inoue T. Kitagawa O. Oda Y. Taguchi T. J. Org. Chem.  1996,  61:  8256 
    Search in Google Scholar
  • 24b Guindon Y. Soucy F. Yoakim C. Ogilvie WW. Plamondon L. J. Org. Chem.  2001,  66:  8992 
    Search in Google Scholar
  • 25 Broeker JL. Hoffmann RW. Houk KN. J. Am. Chem. Soc.  1991,  113:  5006 
    Search in Google Scholar
  • 27 Ramachandran PV. Prabhudas B. Chandra JS. Reddy MVR. J. Org. Chem.  2004,  69:  6294 
    Search in Google Scholar
6

Numbering of atoms throughout article was attributed according to that of zincophorin 1.

26

Ligands on magnesium were not represented for simplicity.