PDF icon PDF herunterladen
Synthesis 2010(21): 3627-3630  
DOI: 10.1055/s-0030-1258248
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Synthesis of (-)-6-Acetoxy-5-hexadecanolide by Organocatalytic α-Oxygenation-Allylation-RCM Strategy

Youngju Park, Jinsung Tae*
Department of Chemistry and Center for Bioactive Molecular Hybrids (CBMH), Yonsei University, Seoul 120-749, Korea
Fax: +82(2)3647050; e-Mail: jstae@yonsei.ac.kr;
Weitere Informationen

Publikationsverlauf

Received 9 July 2010
Publikationsdatum:
07. September 2010 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

An asymmetric total synthesis of (-)-6-acetoxy-5-hexadecanolide has been accomplished by employing a seven-step sequence. Asymmetric α-benzoyloxylation of dodecanal followed by indium-mediated one-pot allylation produces the anti-1,2-diol. The six-membered lactone ring is constructed by RCM reaction.

Key words

allylation - α-benzoyloxylation - metathesis - organocatalysts - total synthesis

    References

  • For recent reviews on organocatalysis, see:
  • 1a Berkessel A. Gröger H. Asymmetric Organocatalysis   Wiley-VCH; Weinheim: 2004. 
  • 1b Dalko PI. Enantioselective Organocatalysis   Wiley-VCH; Weinheim: 2007. 
  • 1c Special issue on organocatalysis (guest editor: List, B.): Chem. Rev.  2007,  107:  5413 
  • 1d Pellissier H. Tetrahedron  2007,  63:  9267 
    Suche in Google Scholar
  • 1e De Figueiredo RM. Christmann M. Eur. J. Org. Chem.  2007,  2575 
  • 1f Dondoni A. Massi A. Angew. Chem. Int. Ed.  2008,  47:  4638 
    Suche in Google Scholar
  • 1g Kotsuki H. Ikishima H. Okuyama A. Heterocycles  2008,  75:  493 
    Suche in Google Scholar
  • 1h Kotsuki H. Ikishima H. Okuyama A. Heterocycles  2008,  75:  757 
    Suche in Google Scholar
  • 1i Enders D. Narine AA. J. Org. Chem.  2008,  73:  7857 
    Suche in Google Scholar
  • 1j Melchiorre P. Marigo M. Carlone A. Bartoli G. Angew. Chem. Int. Ed.  2008,  47:  6138 
    Suche in Google Scholar
  • 1k Bertelsen S. Jørgensen KA. Chem. Soc. Rev.  2009,  38:  2178 
    Suche in Google Scholar
  • 1l Bella M. Gasperi T. Synthesis  2009,  1583 
  • 1m Grondal C. Jeanty M. Enders D. Nat. Chem.  2010,  2:  167 
    Suche in Google Scholar
  • 2 Ramachary DB. Barbas CF. Org. Lett.  2003,  5:  1685 
    CrossrefSuche in Google Scholar
  • 3 Umbreen S. Brockhaus M. Ehrenberg H. Schmidt B. Eur. J. Org. Chem.  2006,  4585 
    Crossref
  • 4a Kotkar SP. Chavan VB. Sudalai A. Org. Lett.  2007,  9:  1001 
    Suche in Google Scholar
  • 4b Zhong G. Yu Y. Org. Lett.  2004,  6:  1637 
    Suche in Google Scholar
  • 5 Yang L. Liu R.-H. Wang B. Weng L.-L. Zheng H. Tetrahedron Lett.  2009,  50:  2628 
    CrossrefSuche in Google Scholar
  • 6a Kim S.-G. Synthesis  2009,  2418 
  • 6b Lim A. Choi JH. Tae J. Tetrahedron Lett.  2008,  49:  4882 
    Suche in Google Scholar
  • 6c Källström S. Erkkilä A. Pihko PM. Sjöholm R. Sillanpää R. Leino R. Synlett  2005,  751 
  • 6d Zhong G. Chem. Commun.  2004,  606 
  • 7a Kano T. Mil H. Maruoka K. J. Am. Chem. Soc.  2009,  131:  3450 
    Suche in Google Scholar
  • 7b Gotoh H. Hayashi Y. Chem. Commun.  2009,  3083 
  • For recent synthesis and leading references, see:
  • 8a Quinn KJ. Curto JM. McGrath KP. Biddick NA. Tetrahedron Lett.  2009,  50:  7121 
    Suche in Google Scholar
  • 8b Singh S. Guiry PJ. Eur. J. Org. Chem.  2009,  1896 
  • 8c Garbe L.-A. Morgenthal K. Kuscher K. Tressl R. Helv. Chim. Acta  2008,  91:  993 
    Suche in Google Scholar
  • 8d Prasad KR. Anbarsan P. Tetrahedron: Asymmetry  2007,  18:  2479 
    Suche in Google Scholar
  • 8e Sabitha G. Swapna R. Reddy EV. Yadav JS. Synthesis  2006,  4242 
  • 8f Ikishima H. Sekiguchi Y. Ichikawa Y. Kotsuki H. Tetrahedron  2006,  62:  311 
    Suche in Google Scholar
  • 8g Dhotare B. Goswami D. Chattopadhyay A. Tetrahedron Lett.  2005,  46:  6219 
    Suche in Google Scholar
  • 8h Sun B. Peng L. Chen X. Li Y. Yamasaki K. Tetrahedron: Asymmetry  2005,  16:  1305 
    Suche in Google Scholar
  • 9a Hayashi Y. Gotoh H. Hayashi T. Shoji M. Angew. Chem. Int. Ed.  2005,  44:  4212 
    Suche in Google Scholar
  • 9b Marigo M. Wabnitz TC. Fielenbach D. Jørgensen KA. Angew. Chem. Int. Ed.  2005,  44:  794 
    Suche in Google Scholar
  • 10a Paquette LA. Mitzel TM. Isaac MB. Crasto CF. Schomer WW. J. Org. Chem.  1997,  62:  4293 
    Suche in Google Scholar
  • 10b Paquette LA. Mitzel TM. J. Am. Chem. Soc.  1996,  118:  1931 
    Suche in Google Scholar
  • For reviews on olefin metathesis, see:
  • 11a Grubbs RH. Chang S. Tetrahedron  1998,  54:  4413 
    Suche in Google Scholar
  • 11b Fürstner A. Angew. Chem. Int. Ed.  2000,  39:  3012 
    Suche in Google Scholar
  • 11c Diver ST. Giessert AJ. Chem. Rev.  2004,  104:  1317 
    Suche in Google Scholar
  • 11d Poulsen CS. Madsen R. Synthesis  2003,  1 
  • 13 Michaelakis A. Mihou APJ. Couladours EA. Zounos AK. Koliopoulos G. J. Agric. Food Chem.  2005,  53:  5225 
    CrossrefSuche in Google Scholar
12

At this point, the minor diastereomer is separated by column chromatography in 15% yield.