Download PDF
Synthesis 2009(21): 3557-3564  
DOI: 10.1055/s-0029-1218152
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of C13-C23 Fragment of Iriomoteolide-1a

Shun-Yi Wang, Yen-Jin Chin, Teck-Peng Loh*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
Fax: +65(6513)8203; e-Mail: teckpeng@ntu.edu.sg;
Further Information

Publication History

Received 8 September 2009
Publication Date:
07 October 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

Highly efficient asymmetric conjugate addition of MeMgBr to α,β-unsaturated esters catalyzed by CuI/Tol-BINAP, Paterson aldol, organocatalytic aldol, and cross-metathesis reactions were applied in the synthesis of C13-C23 fragment of Iriomoteolide-1a.

Key words

asymmetric conjugate addition - organocatalytic aldol - cross-metathesis - Iriomoteolide-1a

    References

  • 1 Tsuda M. Oguchi K. Iwamoto R. Okamoto Y. Kobayashi J. Fukushi E. Kawabata J. Ozawa T. Masuda A. Kitaya Y. Omasa K. J. Org. Chem.  2007,  72:  4469 
    CrossrefPubMedGoogle Scholar
  • 2 Kawabata J. Ozawa T. Masuda A. J. Nat. Prod.  2007,  70:  1661 
    CrossrefGoogle Scholar
  • 3a Review see: Kobayashi J. Tsuda M. Nat. Prod. Rep.  2004,  21:  77 
    Google Scholar
  • 3b Kobayashi J. Kubota T. J. Nat. Prod.  2007,  70:  451 
    Google Scholar
  • For some selected synthesis of amphidinolides, see:
  • 4a Va P. Roush WR. J. Am. Chem. Soc.  2006,  128:  15960 
    Google Scholar
  • 4b Kim CH. An HJ. Shin WK. Yu W. Woo SK. Jung SK. Lee E. Angew. Chem. Int. Ed.  2006,  45:  8019 
    Google Scholar
  • 4c Jin J. Chen Y. Li Y. Wu J. Dai W.-M. Org. Lett.  2007,  9:  2585 
    Google Scholar
  • 5 Fang L. Xue H. Yang J. Org. Lett.  2008,  10:  4645 
    CrossrefPubMedGoogle Scholar
  • 6a Wang S.-Y. Ji S.-J. Loh T.-P. J. Am. Chem. Soc.  2007,  129:  276 
    Google Scholar
  • 6b Wang S.-Y. Lum T.-K. Ji S.-J. Loh T.-P. Adv. Synth. Catal.  2008,  350:  673 
    Google Scholar
  • 7 Lum T.-K. Wang S.-Y. Loh T.-P. Org. Lett.  2008,  10:  761 
    CrossrefPubMedGoogle Scholar
  • 8 For asymmetric addition of Grignard reagents to α,β-unsaturated thioesters, see: Macia Ruiz B. Geurts K. Fernandez-Ibanez MA. ter Horst B. Minnaard AJ. Feringa BL. Org. Lett.  2007,  9:  5123 
    CrossrefGoogle Scholar
  • 9 For asymmetric addition of Grignard reagents to sulfones, see: Bos PH. Minnaard AJ. Feringa BL. Org. Lett.  2008,  10:  4219 
    CrossrefGoogle Scholar
  • 10 Bates RW. Sridhar S. J. Org. Chem.  2008,  73:  8104 
    CrossrefPubMedGoogle Scholar
  • 11a Paterson I. Wallace DJ. Velázquez SM. Tetrahedron Lett.  1994,  35:  9083 
    Google Scholar
  • 11b Paterson I. Wallace DJ. Cowden CJ. Synthesis  1998,  639 
    Google Scholar
  • 11c Cowden CJ. Paterson I. Org. React.  1997,  51:  1 
    Google Scholar
  • 13a Notz W. List B. J. Am. Chem. Soc.  2000,  122:  7386 
    Google Scholar
  • 13b

    The absolute configuration of 22 was determined based on this reference.

  • 14a Garber SB. Kingsbury JS. Gray BL. Hoveyda AH. J. Am. Chem. Soc.  2000,  122:  8168 
    Google Scholar
  • 14b Hoye TR. Zhao H. Org. Lett.  1999,  1:  1123 
    Google Scholar
  • 14c Chatterjee AK. Choi T.-L. Sanders DP. Grubbs RH. J. Am. Chem. Soc.  2003,  125:  11360 
    Google Scholar
  • 15 For an example of CM reactions between olefins bearing a quartenary carbon atom and an α-olefin in the total synthesis of a natural product, see: Kanada RM. Itoh D. Nagai M. Niijima J. Asai N. Mizui Y. Abe S. Kotake Y. Angew. Chem. Int. Ed.  2007,  46:  4350 
    CrossrefGoogle Scholar
12

Private communication with Professor Ian Paterson.