Download PDF
Synthesis 2010(15): 2643-2651  
DOI: 10.1055/s-0029-1218825
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of the C1-C14 Fragment of Sarcoglaucol-16-one via Z-Selective Ando-Type Horner-Wadsworth-Emmons Olefination

Christoph Gastl, Sabine Laschat*
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany
Fax: +49(711)68564285; e-Mail: sabine.laschat@oc.uni-stuttgart.de;
Further Information

Publication History

Received 26 March 2010
Publication Date:
18 June 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

A synthetic strategy involving a Z-selective Horner-Wadsworth-Emmons olefination was developed for the preparation of the sarcoglaucolone precursor methyl (2Z,6E)-8-(methoxymeth­oxy)-6-methyl-2-[(3E)-4-methyl-5-oxopent-3-enyl]-9-[(trimethylsilyl)methyl]deca-2,6,9-trienoate. The target compound was isolated in a E/Z ratio of 17:83

Key words

Ando-type reaction - olefination - cembranolide - natural product - macrocycles

    References

  • For reviews, see:
  • 1a Hanson JR. Nat. Prod. Rep.  2006,  23:  875 
    Google Scholar
  • 1b Hanson JR. Nat. Prod. Rep.  2005,  22:  594 
    Google Scholar
  • 1c Uyehara T. Yamamoto Y. Chemtracts: Org. Chem.  1988,  1:  273 
    Google Scholar
  • 1d Tius MA. Chem. Rev.  1988,  88:  719 
    Google Scholar
  • For recent isolations, see:
  • 2a Cheng S.-Y. Wen Z.-H. Wang S.-K. Chiou S.-F. Hsu C.-H. Dai C.-F. Chiang MY. Duh C.-Y. J. Nat. Prod.  2009,  72:  152 
    Google Scholar
  • 2b Cheng S.-Y. Wen Z.-H. Chiou S.-F. Hsu C.-H. Wang S.-K. Dai C.-F. Chiang MY. Duh C.-Y. Tetrahedron  2008,  64:  9698 
    Google Scholar
  • 2c Chen S.-H. Guo Y.-W. Huang H. Cimino G. Helv. Chim. Acta  2008,  91:  873 
    Google Scholar
  • 2d Marrero J. Benitez J. Rodriguez AD. Zhao H. Raptis RG. J. Nat. Prod.  2008,  71:  381 
    Google Scholar
  • 2e Dorta E. Diaz-Morrero AR. Brito I. Cueto M. D’Croz L. Darias J. Tetrahedron  2007,  63:  9057 
    Google Scholar
  • 2f Desoubzdanne D. Marcourt L. Raux R. Chevalley S. Dorin D. Doerig C. Valentin A. Ausseil F. Debitus C. J. Nat. Prod.  2008,  71:  1189 
    Google Scholar
  • 2g Kamel HN. Ferreira D. Garcia-Fernandez LF. Slattery M. J. Nat. Prod.  2007,  70:  1223 
    Google Scholar
  • 2h Wang L.-T. Wang S.-K. Soong K. Duh C.-Y. Chem. Pharm. Bull.  2007,  55:  766 
    Google Scholar
  • 2i Yan X.-H. Gavagnin M. Cimino G. Guo Y.-W. Tetrahedron Lett.  2007,  48:  5313 
    Google Scholar
  • 2j Nieto MI. Gonzalez N. Rodriguez J. Kerr RG. Jimenez C. Tetrahedron  2006,  62:  11747 
    Google Scholar
  • 2k Su J.-H. Ahmed AF. Sung P.-J. Chao C.-H. Shen J.-H. J. Nat. Prod.  2006,  69:  1134 
    Google Scholar
  • 2l Jia R. Guo Y.-W. Mollo E. Gavagnin M. Cimino G. J. Nat. Prod.  2006,  69:  819 
    Google Scholar
  • For recent synthetic approaches, see:
  • 3a Tietze LF. Brazel CC. Hölsken S. Magull J. Ringe A. Angew. Chem. Int. Ed.  2008,  47:  5246 ; Angew. Chem. 2008, 120, 5324
    Google Scholar
  • 3b Schweizer E. Gaich T. Brecker L. Mulzer J. Synthesis  2007,  3807 
    Google Scholar
  • 3c Wipf P. Grenon M. Can. J. Chem.  2006,  84:  1226 
    Google Scholar
  • 3d Katsuyama I. Fahmy H. Zjawiony JK. Khalifa SI. Kilada RW. Konoshima T. Takasahi M. Tokuda H. J. Nat. Prod.  2002,  65:  1809 
    Google Scholar
  • 4a Marshall JA. Van Devender EA. J. Org. Chem.  2001,  66:  8037 
    Google Scholar
  • 4b Marshall JA. Gung BW. Isr. J. Chem.  1991,  31:  199 
    Google Scholar
  • 4c Marshall JA. Markwalder JA. Tetrahedron Lett.  1988,  29:  4811 
    Google Scholar
  • 4d Marshall JA. DeHoff BS. J. Org. Chem.  1986,  51:  863 
    Google Scholar
  • 5 Gross H. Wright AD. Beil W. König GM. Org. Biomol. Chem.  2004,  2:  1133 
    CrossrefGoogle Scholar
  • 6 For an excellent review on α-methylene-γ-butyrolactones, see: Kitson RRA. Millemaggi A. Taylor RJK. Angew. Chem. Int. Ed.  2009,  48:  9426 ; Angew. Chem. 2009, 121, 9590
    CrossrefGoogle Scholar
  • 7 Umbreit MA. Sharpless KB. J. Am. Chem. Soc.  1977,  99:  5526 
    CrossrefGoogle Scholar
  • 8 Watanabe Y. Laschat S. Budde M. Affolter O. Shimada Y. Urlacher VB. Tetrahedron  2007,  63:  9413 
    CrossrefGoogle Scholar
  • 9 Seifert A. Vormund S. Grohmann K. Kriening S. Urlacher VB. Laschat S. Pleiss J. ChemBioChem  2009,  10:  853 
    CrossrefPubMedGoogle Scholar
  • For reviews, see:
  • 10a Hoveyda AH. Malcolmson SJ. Meek SJ. Zhugralin AR. Angew. Chem. Int. Ed.  2010,  49:  434 ; Angew. Chem. 2010, 122, 38
    Google Scholar
  • 10b Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed.  2005,  44:  4490 ; Angew. Chem. 2005, 117, 4564
    Google Scholar
  • 10c Fürstner A. Angew. Chem. Int. Ed.  2000,  39:  3012 ; Angew. Chem. 2000, 112, 3140
    Google Scholar
  • 11 For a recent example, see: Fuwa H. Naito S. Goto T. Sasaki M. Angew. Chem. Int. Ed.  2008,  47:  4737 ; Angew. Chem. 2008, 120, 4815
    CrossrefGoogle Scholar
  • 12 For a review, see: Hosomi A. Acc. Chem. Res.  1988,  21:  200 
    CrossrefGoogle Scholar
  • 13a Ishihara K. Mouri M. Gao Q. Maruyama T. Furuta K. Yamamoto H. J. Am. Chem. Soc.  1993,  115:  11490 
    Google Scholar
  • 13b Hosomi A. Hashimoto H. Kobayashi H. Sakurai H. Chem. Lett.  1979,  8:  245 
    Google Scholar
  • 13c Hosomi A. Sakurai H. Tetrahedron Lett.  1976,  17:  1295 
    Google Scholar
  • 14 Kitamura M. Suga S. Kawai K. Noyori R. J. Am. Chem. Soc.  1986,  108:  6072 
    CrossrefGoogle Scholar
  • 15 Blanchette MA. Choy W. Davis JT. Essenfeld A. Masamune S. Roush WR. Sakui T. Tetrahedron Lett.  1984,  25:  2183 
    CrossrefGoogle Scholar
  • 16 Daniewski AR. Wojceichowska W. J. Org. Chem.  1982,  47:  2993 
    CrossrefGoogle Scholar
  • For reviews, see:
  • 17a Marshall JA. J. Org. Chem.  2007,  72:  8153 
    Google Scholar
  • 17b Noyori R. Kitamura M. Angew. Chem., Int. Ed. Engl.  1991,  30:  34 ; Angew. Chem. 1991, 103, 34
    Google Scholar
  • 17c Tomioka K. Synthesis  1990,  541 
    Google Scholar
  • 18 Petrier C. Barbosa JDS. Dupuy C. Luche JL. J. Org. Chem.  1985,  50:  5761 
    Google Scholar
  • 19 Nugent WA. Chem. Commun.  1999,  1369 
    CrossrefGoogle Scholar
  • 20 Trost BM. Greve TA. Chan DMT. J. Am. Chem. Soc.  1991,  113:  7350 
    CrossrefGoogle Scholar
  • 21 Masui M. Shiori T. Tetrahedron  1995,  51:  8363 
    CrossrefGoogle Scholar
  • 22a Ando K. J. Org. Chem.  1999,  64:  8406 
    Google Scholar
  • 22b Ando K.
    J. Org. Chem.  1997,  62:  1934 
    Google Scholar
  • 23 Veysoglu T. Mitscher LA. Swayze JK. Synthesis  1980,  807 
    Article in Thieme ConnectGoogle Scholar
  • 24 Phoenix S. Bourque E. Deslongchamps P. Org. Lett.  2000,  2:  4149 
    CrossrefGoogle Scholar
  • 25 Pihko PM. Saloa TM. Tetrahedron Lett.  2003,  44:  4361 
    CrossrefGoogle Scholar
  • 26 Ando K. Oishi T. Hirama M. Ohno H. Ibuha T. J. Org. Chem.  2000,  65:  4745 
    CrossrefPubMedGoogle Scholar
  • 27 Still WC. Gennari C. Tetrahedron Lett.  1983,  24:  4405 
    CrossrefGoogle Scholar