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Synlett 2008(18): 2831-2835  
DOI: 10.1055/s-0028-1083542
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Prolinamide/PPTS-Catalyzed Hajos-Parrish Annulation: Efficient Approach to the Tricyclic Core of Cylindricine-Type Alkaloids

Xiao-Ming Zhang, Min Wang, Yong-Qiang Tu*, Chun-An Fan, Yi-Jun Jiang, Shu-Yu Zhang, Fu-Min Zhang*
State Key Laboratory of Applied Organic Chemistry & Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: tuyq@lzu.edu.cn;
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Publication History

Received 20 June 2008
Publication Date:
15 October 2008 (online)

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Abstract

A series of Wieland-Miescher ketone analogues bearing highly functionalized substituents are efficiently constructed in high enantioselectivities and good yields using catalytic amounts of prolinamide and PPTS. We have successfully utilized this reaction as a key step to synthesize the tricyclic core of cylindricine type alkaloids.

Key words

prolinamide - Hajos-Parrish annulation - Wieland-Miescher ketone analogues - cylindricine type alkaloids - intramolecular Schmidt reaction

    References and Notes

  • For recent instance, see:
  • 1a Kaliappan KP. Ravikumar V. Org. Lett.  2007,  9:  2417 
    Google Scholar
  • 1b Lanfranchi DA. Hanquet G. J. Org. Chem.  2006,  71:  4854 
    Google Scholar
  • 1c González SA. Bradshaw BJ. Bonjoch CJ. J. Org. Chem.  2005,  70:  3749 
    Google Scholar
  • 1d Hagiwara H. Hamano K. Nozawa M. Hoshi T. Suzuki T. Kido F. J. Org. Chem.  2005,  70:  2250 
    Google Scholar
  • 1e Shigehisa H. Mizutani T. Tosaki S. Ohshima T. Shibasaki M. Tetrahedron  2005,  61:  5057 
    Google Scholar
  • 1f Kanoh N. Smith ABIII. Ishiyama H. Minakawa N. Rainier JD. Hartz RA. Cho YS. Cui H. Moser WH. J. Am. Chem. Soc.  2003,  125:  8228 
    Google Scholar
  • 1g Suzuki A. Nakatani M. Nakamura M. Kawaguchi K. Inoue M. Katoh T. Synlett  2003,  329 
    Google Scholar
  • 1h Deng W.-P. Zhong M. Guo X.-C. Kende AS. J. Org. Chem.  2003,  68:  7422 
    Google Scholar
  • 1i Ling T. Chowdhury C. Kramer BA. Vong BG. Palladino MA. Theodorakis EA. J. Org. Chem.  2001,  66:  8843 
    Google Scholar
  • 2a Wieland P. Miescher K. Helv. Chim. Acta  1950,  33:  2215 
    Google Scholar
  • 2b Hajos ZG. Parrish DR. J. Org. Chem.  1974,  39:  1615 
    Google Scholar
  • 2c Eder U. Sauer G. Wiechert R. Angew. Chem., Int. Ed. Engl.  1971,  10:  496 
    Google Scholar
  • 3a Davies SG. Russell AJ. Sheppard RL. Smith AD. Thomson JE. Org. Biomol. Chem.  2007,  5:  3190 
    Google Scholar
  • 3b He L. Hecheng Huaxue  2007,  15:  231 
    Google Scholar
  • 3c Sulzer-Mossé S. Laars M. Kriis K. Kanger T. Alexakis A. Synthesis  2007,  1729 
    Google Scholar
  • 3d Kanger T. Kriis K. Laars M. Kailas T. Müürisepp A.-M. Pehk T. Lopp M. J. Org. Chem.  2007,  72:  5168 
    Google Scholar
  • 3e Lacoste E. Vaique E. Berlande M. Pianet I. Vincent J.-M. Landais Y. Eur. J. Org. Chem.  2007,  167 
    Google Scholar
  • 3f Nagamine T. Inomata K. Endo Y. Paquette LA. J. Org. Chem.  2007,  72:  123 
    Google Scholar
  • 3g Kriis K. Kanger T. Laars M. Kailas T. Müürisepp A.-M. Pehk T. Lopp M. Synlett  2006,  1699 
    Google Scholar
  • 3h Kasai Y. Shimanuki K. Kuwahara S. Watanabe M. Harada N. Chirality  2006,  18:  177 
    Google Scholar
  • 3i Davies SG. Sheppard RL. Smith AD. Thomson JE. Chem. Commun.  2005,  3802 
    Google Scholar
  • 3j Cheong PH. Houk KN. Warrier JS. Hanessian S. Adv. Synth. Catal.  2004,  346:  1111 
    Google Scholar
  • 3k Fuhshuku K.-I. Tomita M. Sugai T. Adv. Synth. Catal.  2003,  345:  766 
    Google Scholar
  • 3l Lo L.-C. Shie J.-J. Chou T.-C. J. Org. Chem.  2002,  67:  282 
    Google Scholar
  • 3m Hioki H. Hashimoto T. Kodama M. Tetrahedron: Asymmetry  2000,  11:  829 
    Google Scholar
  • 3n Fuhshuku K.-I. Funa N. Akeboshi T. Ohta H. Hosomi H. Ohba S. Sugai T. J. Org. Chem.  2000,  65:  129 
    Google Scholar
  • 3o Bui T. Barbas CF. Tetrahedron Lett.  2000,  41:  6951 
    Google Scholar
  • 4 Gu P. Zhao Y.-M. Tu YQ. Ma Y. Zhang F. Org. Lett.  2006,  8:  5271 
    CrossrefGoogle Scholar
  • 5a Hiroya K. Takahashi T. Shimomae K. Sakamoto T. Chem. Pharm. Bull.  2005,  53:  207 
    Google Scholar
  • 5b Ziegler FE. Wallace OB. J. Org. Chem.  1995,  60:  3626 
    Google Scholar
  • 6 Ramachary DB. Kishor M. J. Org. Chem.  2007,  72:  5056 
    CrossrefGoogle Scholar
  • 7a Inomata K. Barrague M. Paquette LA. J. Org. Chem.  2005,  70:  533 
    Google Scholar
  • 7b Hanselmann R. Benn M. Synth. Commun.  1996,  26:  945 
    Google Scholar
  • For very recent instance of prolinamide catalytic aldol reaction, see:
  • 8a Guillena G. Hita M. Nájera C. Viózquez SF. Tetrahedron: Asymmetry  2007,  18:  2300 
    Google Scholar
  • 8b Russo A. Botta G. Lattanzi A. Tetrahedron  2007,  63:  11886 
    Google Scholar
  • 8c Tang Z. Marx A. Angew. Chem. Int. Ed.  2007,  46:  7297 
    Google Scholar
  • 8d Hong B. Wu M. Tseng H. Huang G. Su C. Liao J. J. Org. Chem.  2007,  72:  8459 
    Google Scholar
  • 8e Peng Y. Liu H. Cui M. Cheng J. Chin. J. Chem.  2007,  25:  962 
    Google Scholar
  • 8f Dodda R. Zhao C. Synlett  2007,  1605 
    Google Scholar
  • 8g Guillena G. Hita MC. Nájera C. Tetrahedron: Asymmetry  2007,  18:  1272 
    Google Scholar
  • 8h Aratake S. Itoh T. Okano T. Usui T. Shoji M. Hayashi Y. Chem. Commun.  2007,  2524 
    Google Scholar
  • 8i Zhang F. Peng Y. Liao S. Gong Y. Tetrahedron  2007,  63:  4636 
    Google Scholar
  • 8j Ma G. Zhang Y. Shi M. Synthesis  2007,  197 
    Google Scholar
  • 9 Hayashi Y. Yamaguchi J. Hibino K. Sumiya T. Urushima T. Shoji M. Hashizume D. Koshino H. Adv. Synth. Catal.  2004,  346:  1435 
    CrossrefGoogle Scholar
  • 10a Tang Z. Cun L.-F. Cui X. Mi A.-Q. Jiang Y.-Z. Gong L.-Z. Org. Lett.  2006,  8:  1263 
    Google Scholar
  • 10b Cobb AJA. Shaw DM. Longbottom DA. Gold JB. Ley SV. Org. Biomol. Chem.  2005,  3:  84 
    Google Scholar
  • 10c Berkessel A. Koch B. Lex J. Adv. Synth. Catal.  2004,  346:  1141 
    Google Scholar
  • 11 Rajamannar T. Balasubramanian KK. Synth. Commun.  1994,  24:  279 
    CrossrefGoogle Scholar
  • 12a Blackman AJ. Li C. Hockless DCR. Skelton BW. White AH. Tetrahedron  1993,  49:  8645 
    Google Scholar
  • 12b Li C. Blackman AJ. Aust. J. Chem.  1994,  47:  1355 
    Google Scholar
  • 12c Li C. Blackman AJ. Aust. J. Chem.  1995,  48:  955 
    Google Scholar
  • 13a Biard JF. Guyot S. Roussakis C. Verbist JF. Vercauteren J. Weber JF. Boukef K. Tetrahedron Lett.  1994,  35:  2691 
    Google Scholar
  • 13b Juge M. Grimaud N. Biard JF. Sauviat MP. Nabil M. Verbist JF. Petit JY. Toxicon  2001,  39:  1231 
    Google Scholar
  • 13c Sauviat MP. Vercauteren J. Grimaud N. Juge M. Nabil M. Petit JY. Biard JF.
    J. Nat. Prod.  2006,  69:  558 
    Google Scholar
  • For a review and some recent work on the total synthesis of cylindricines and lepadiformine, see:
  • 14a Weinreb SM. Chem. Rev.  2006,  106:  2531 
    Google Scholar
  • 14b Caldwell JJ. Craig D. Angew. Chem. Int. Ed.  2007,  119:  2685 
    Google Scholar
  • 14c Flick AC. Caballero MJA. Padwa A. Org. Lett.  2008,  10:  1871 
    Google Scholar
  • 15a Aubé J. Milligan GL. J. Am. Chem. Soc.  1991,  113:  8965 
    Google Scholar
  • 15b Milligan GL. Mossman CJ. Aubé J. J. Am. Chem. Soc.  1995,  117:  10449 
    Google Scholar
  • 15c Iyengar R. Schildknegt K. Aubé J. Org. Lett.  2000,  2:  1625 
    Google Scholar
  • 17a Kabalka GW. Yu S. Li NS. Tetrahedron Lett.  1997,  38:  5455 
    Google Scholar
  • 17b Kabalka GW. Yu S. Li NS. Can. J. Chem.  1998,  76:  800 
    Google Scholar
  • 18 Greene TW. Wuts PGM. Protective Groups in Organic Synthesis   3rd ed.:  Wiley; New York: 1999.  Chap. 4.
    Google Scholar
  • 19 Thomsen I. Clausen K. Scheibye S. Lawesson S.-O. Org. Synth.  1984,  62:  158 
    CrossrefGoogle Scholar
16

See ref. 3e; we had increased the yield to 65% over two steps by using H2O-AcOH (100:1.5) as the solvent and 2 equiv of MVK under reflux conditions in the second step.

20

CCDC 696349 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.