Download PDF
Synthesis 2011(7): 1055-1058  
DOI: 10.1055/s-0030-1258453
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Formal Synthesis of (R)-(+)-Lasiodiplodin

Yange Huang, Adriaan J. Minnaard*, Ben L. Feringa*
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
Fax: +31(50)3634278; e-Mail: a.j.minnaard@rug.nl; e-Mail: b.l.feringa@rug.nl;
Further Information

Publication History

Received 22 November 2010
Publication Date:
01 March 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

A catalytic approach is reported for the enantioselective synthesis of (R)-(+)-lasiodiplodin methyl ether using asymmetric hetero allylic alkylation as the key step.

Key words

formal synthesis - lasiodiplodin - asymmetric allylic alkylation - Suzuki coupling - ring-closing metathesis

    References

  • 1a Delmotte P. Delmotte-Plaquee J. Nature  1953,  171:  344 
    Google Scholar
  • 1b Stob M. Baldwin RSK. Gillette G. Andrews F. Tuite NJ. Nature  1962,  196:  1318 
    Google Scholar
  • 1c Ellestad GA. Lovell FMN. Perkinson A. Hargreaves RT. McGahren WJ. J. Org. Chem.  1978,  43:  2339 
    Google Scholar
  • 1d Nair MSR. Carey ST. Tetrahedron Lett.  1980,  21:  2011 
    Google Scholar
  • 2a Aldridge DC. Galt S. Giles D. Turner B. J. Chem. Soc. C  1971,  1623 
    Google Scholar
  • 2b Cambie RC. Lal AR. Rutledge PS. Woodgate PD. Phytochemistry  1991,  30:  287 
    Google Scholar
  • 2c Lee K.-H. Hayashi N. Okano M. Hall IH. Wu R.-Y. McPhail AT. Phytochemistry  1982,  21:  1119 
    Google Scholar
  • 3 Xin-Sheng Y. Ebizuka Y. Noguchi H. Kiuchi F. Litaka Y. Sankawa U. Seto H. Tetrahedron Lett.  1983,  2407 
    Google Scholar
  • 4a Gerlach H. Thalmann A. Helv. Chim. Acta  1977,  60:  2866 
    Google Scholar
  • 4b Danishefsky SJ. Etheredge SJ. J. Org. Chem.  1979,  44:  4716 
    Google Scholar
  • 4c Takahashi T. Kasuga K. Tsuji J. Tetrahedron Lett.  1978,  4917 
    Google Scholar
  • 4d Braun M. Mahler U. Houben S. Liebigs Ann. Chem.  1990,  513 
    Google Scholar
  • 4e Jones GB. Huber RS. Synlett  1993,  367 
    Google Scholar
  • 4f Fink M. Gaier H. Gerlach H. Helv. Chim. Acta  1982,  65:  2563 
    Google Scholar
  • 4g Solladie G. Rubio A. Carreno MC. Ruano JLG. Tetrahedron: Asymmetry  1990,  1:  187 
    Google Scholar
  • 4h Bracher F. Schulte B. J. Chem. Soc., Perkin Trans. 1  1996,  2619 
    Google Scholar
  • 4i Fürstner A. Seidel G. Kindler N. Tetrahedron  1999,  55:  8215 
    Google Scholar
  • 4j Fürstner A. Thiel OR. Kindler N. Bartkowska B. J. Org. Chem.  2000,  65:  7990 
    Google Scholar
  • 4k Kashima T. Takahashi K. Matsuura H. Nabeta K. Biosci., Biotechnol., Biochem.  2009,  73:  1118 
    Google Scholar
  • 4l Kashima T. Takahashi K. Matsuura H. Nabeta K. Biosci., Biotechnol., Biochem.  2009,  73:  2522 
    Google Scholar
  • 4m Fürstner A. Kindler N. Tetrahedron Lett.  1996,  37:  7005 
    Google Scholar
  • 5 Geurts K. Fletcher SP. Feringa BL. J. Am. Chem. Soc.  2006,  128:  15572 
    CrossrefGoogle Scholar
  • 6 Abe H. Nishioka K. Takeda S. Arai M. Takeuchi Y. Harayama T. Tetrahedron Lett.  2005,  46:  3197 
    CrossrefGoogle Scholar
  • 7 Chemler SR. Trauner D. Danishefsky SJ. Angew. Chem. Int. Ed.  2001,  40:  4544 
    Google Scholar
  • 8 Wong LS.-M. Sherburn MS. Org. Lett.  2003,  5:  3603 
    CrossrefGoogle Scholar
  • 9 Fürstner A. Bindl M. Jean L. Angew. Chem. Int. Ed.  2007,  46:  9275 
    Google Scholar
  • 10 Olah GA. Nojima M. Kerekes I. Synthesis  1973,  487 
    Article in Thieme ConnectGoogle Scholar
  • 11 Crimmins MT. Tabet EA. J. Am. Chem. Soc.  2000,  122:  5473 
    CrossrefGoogle Scholar
  • 12 Quinn KJ. Curto JM. McGrath KP. Biddick NA. Tetrahedron Lett.  2009,  50:  7121 
    CrossrefGoogle Scholar
13

The final product 5 appears to be unstable upon storing at room temperature.