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Synlett 2010(2): 247-249  
DOI: 10.1055/s-0029-1218572
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Stereocontrolled Synthesis of (±)-Ptilocaulin via a Rh(I)-Catalyzed Intramolecular [4+2] Cycloaddition

Kaisheng Shen, Tom Livinghouse*
Department of Chemistry and Biochemistry, 103 CBB, Montana State University, Bozeman, MT 59717, USA
Fax: +1(406)9945407; e-Mail: livinghouse@chemistry.montana.edu;
Further Information

Publication History

Received 9 September 2009
Publication Date:
17 December 2009 (online)

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Abstract

A stereospecific Rh(I)-catalyzed intramolecular [4+2] cycloaddition has been used to elaborate the essential carbocyclic core of (±)-ptilocaulin.

Key words

cycloaddition reactions - transition-metal catalysts - rhodium(I)

    References and Notes

  • 1 Lautens M. Klute W. Tam W. Chem. Rev.  1996,  96:  49 
    Google Scholar
  • 2a Wender PA. Gamber GG. Hubbard RD. Zhang L. J. Am. Chem. Soc.  2002,  124:  2876 
    Google Scholar
  • 2b Wender PA. Glorius F. Husfeld CO. Langkopf E. Love JA. J. Am. Chem. Soc.  1999,  121:  5348 
    Google Scholar
  • 2c Trost BM. Toste FD. Shen H. J. Am. Chem. Soc.  2000,  122:  2379 
    Google Scholar
  • 2d Wender PA. Smith TE. Tetrahedron  1998,  54:  1255 
    Google Scholar
  • 2e Takacs JM. Zhu J. Chandramouli S. J. Am. Chem. Soc.  1992,  114:  773 
    Google Scholar
  • 2f Trost BM. Toste FD. Shen H. J. Am. Chem. Soc.  2000,  122:  2379 
    Google Scholar
  • 2g Wender PA. Deschamps NM. Gamber GG. Angew. Chem. Int. Ed.  2003,  42:  1853 
    Google Scholar
  • 2h Wender PA. Christy JP. J. Am. Chem. Soc.  2006,  128:  5354 
    Google Scholar
  • 2i Wang W. Wang J. Su J. Huang F. Jiao L. Liang Y. Yang D. Zhang S. Wender PA. Yu Z.-X. J. Am. Chem. Soc.  2007,  129:  10060 
    Google Scholar
  • 2j Yu RT. Rovis T. J. Am. Chem. Soc.  2006,  128:  2782 
    Google Scholar
  • 3a Jolly RS. Luedtke G. Sheehan D. Livinghouse T. J. Am. Chem. Soc.  1990,  112:  4965 
    Google Scholar
  • 3b McKinstry L. Livinghouse T. Tetrahedron  1994,  50:  6145 
    Google Scholar
  • 3c O’Mahony DJR. Belanger DB. Livinghouse T. Synlett  1998,  443 
    Google Scholar
  • 3d Heath H. Wolfe B. Livinghouse T. Bae SK. Synthesis  2001,  2341 
    Google Scholar
  • 3e O’Mahony DJR. Belanger DB. Livinghouse T. Org. Biomol. Chem.  2003,  1:  2038 
    Google Scholar
  • 4 Harbour GC. Tymiak AA. Reinhart KL. Shaw PD. Hughes RG. Mizsak SA. Coats JH. Zurenco GE. Li LH. Kuentzel SL. J. Am. Chem. Soc.  1981,  103:  5604 
    CrossrefGoogle Scholar
  • 5 Ruben RI. Snider BB. Hobbs FW. Confalone PN. Dusak BA. Invest. New Drugs  1989,  7:  147 
    Google Scholar
  • 6a Snider BB. Faith WC. J. Am. Chem. Soc.  1984,  106:  1443 
    Google Scholar
  • 6b Uyehara T. Furuta T. Kabawawa Y. Yamada J.-I. Kato T. Yamamoto Y. J. Org. Chem.  1988,  53:  3669 
    Google Scholar
  • 6c Roush WR. Walts AE. J. Am. Chem. Soc.  1984,  106:  721 
    Google Scholar
  • 6d Hassner A. Keshava Murthy KS. Tetrahedron Lett.  1986,  27:  1407 
    Google Scholar
  • 6e Hassner A. Keshava Murthy KS. Isr. J. Chem.  1991,  31:  239 
    Google Scholar
  • 6f Asaoka M. Sakurai M. Takei H. Tetrahedron Lett.  1990,  31:  4759 
    Google Scholar
  • 6g Cossy J. BouzBouz S. Tetrahedron Lett.  1996,  37:  5091 
    Google Scholar
  • 6h Schmalz H.-G. Schellhaas K. Angew. Chem., Int. Ed. Engl.  1996,  35:  2146 
    Google Scholar
  • 6i Schellhaas K. Schmalz H.-G. Bats JW. Chem. Eur. J.  1998,  4:  57 
    Google Scholar
  • 6j For the syntheses of additional members belonging to this alkaloid family, see: Min Y. Pochapsky SS. Snider BB. J. Org. Chem.  2008,  73:  9065 
    Google Scholar
  • 7a Green C. Hickinbottom WJ. J. Chem. Soc.  1957,  3270 
    Google Scholar
  • 7b

    The authors would like to thank Ms. Elisa Sunsdahl for optimizing the large-scale preparation of 2.

  • 8 Uenishi J. Kawahama R. Yonemitsu O. Tsuji J. J. Org. Chem.  1998,  63:  8965 
    CrossrefGoogle Scholar