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Synthesis 2012(2): 297-303  
DOI: 10.1055/s-0031-1289648
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Concise and Diastereoselective Synthesis of Piperidine and Indolizidine Alkaloids via Aza-Prins Cyclization

Basi V. Subba Reddy*a, Dudhmal N. Chayaa, Jhillu S. Yadava, René Gréeb
a Discovery Laboratory, Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: basireddy@iict.res.in; e-Mail: bvsreddiict@gmail.com;
b Université de Rennes 1, Laboratoire SCR, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France
Further Information

Publication History

Received 27 September 2011
Publication Date:
15 December 2011 (online)

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Abstract

The synthesis of 2-substituted and 2,4-disubstituted piperidine alkaloids such as (±)-coniine, (±)-hydroxypipecolic acid, (±)-pipecolic acid, (±)-coniceine, and (±)-4-hydroxy-2-hydroxy­methyl piperidine have been accomplished in a highly diastereo­selective manner by employing aza-Prins cyclization as a key step to construct the piperidine core of these alkaloids.

Key words

aza-Prins cyclization - diastereoselective - piperidine - alkaloids - natural products

    References and Notes

  • 1a Jones TH. Blum MS. In Alkaloids: Chemical and Biological Perspectives   Vol. 1:  Pelletier SW. Wiley; New York: 1983.  Chap. 2. p.33 
    Search in Google Scholar
  • 1b Fodor GB. Colasanti B. In Alkaloids: Chemical and Biological Perspectives   Vol. 3:  Pelletier SW. Wiley; New York: 1985.  Chap. 1. p.1-90  
    Search in Google Scholar
  • 1c Schneider MJ. In Alkaloids: Chemical and Biological Perspectives   Vol. 10:  Pelletier SW. Wiley; New York: 1986.  Chap. 3. p.155 
    Search in Google Scholar
  • 1d Trunz GM. Findlay JA. In The Alkaloids   Brossi A. Academic; London: 1985.  Chap. 3. p.89 
  • 1e Numata A. Ibuka I. In The Alkaloids   Vol. 31:  Brossi A. Academic; New York: 1987.  p.193 
    Search in Google Scholar
  • 1f Angle RS. Breitenbucher JG. Studies in Natural Products Chemistry, In Stereoselective Synthesis (Part J)   Vol. 16:  . Elsevier; Amsterdam: 1995.  p.453 
    Search in Google Scholar
  • 1g Gershwin ME. Terr A. Clin. Rev. Allergy Immunol.  1996,  14:  241 
    Search in Google Scholar
  • 1h Micel KH. Sandberg F. Haglid F. Norin T. Acta Pharm. Suec.  1967,  4:  97 
    Search in Google Scholar
  • 1i Micel KH. Sandberg F. Haglid F. Norin T. Chan RPK. Craig JC. Acta Chem. Scand.  1969,  23:  3479 
    Search in Google Scholar
  • 1j Kallstrom S. Leino R. Bioorg. Med. Chem.  2008,  16:  601 
    Search in Google Scholar
  • 2a Wenzel B. Sorger D. Heinitz K. Scheunemann M. Schliebs R. Steinbach J. Sabri O. Eur. J. Med. Chem.  2005,  40:  1197 
    Search in Google Scholar
  • 2b Guzikowski AP. Tamiz AP. Acosta-Burruel M. Hong-Bae S. Cai SX. Hawkinson JE. Keana JF. Kesten SR. Shipp CT. Tran M. Whittermore ER. Woodward RM. Wright JL. Zhou ZL. J. Med. Chem.  2000,  43:  984 ; and references cited therein
    Search in Google Scholar
  • 2c Watson AA. Fleet GWJ. Asano N. Molyneux RJ. Nash RJ. Phytochemistry  2001,  56:  265 
    Search in Google Scholar
  • 2d Daly JW. Spande TF. Garraffo HM. J. Nat. Prod.  2005,  68:  1556 
    Search in Google Scholar
  • 2e Asano N. Curr. Top. Med. Chem.  2003,  3:  471 
    Search in Google Scholar
  • 2f Howard N. Abell C. Blakemore W. Chessari G. Congreve M. Howard S. Jhoti H. Murray CW. Seavers LCA. Van Montfort RLM. J. Med. Chem.  2006,  49:  1346 
    Search in Google Scholar
  • 2g Zhou Y. Gregor VE. Ayida BK. Winters GC. Sun Z. Murphy D. Haley G. Bailey D. Froelich JM. Fish S. Webber SE. Hermann T. Wall D. Bioorg. Med. Chem. Lett.  2007,  17:  1206 
    Search in Google Scholar
  • 2h Baliah V. Jeyaraman R. Chandrasekaran L. Chem. Rev.  1983,  83:  379 
    Search in Google Scholar
  • 2i Horton DA. Bourne GT. Smythe ML. Chem. Rev.  2003,  103:  893 
    Search in Google Scholar
  • 2j Michael JP. Nat. Prod. Rep.  2008,  25:  139 
    Search in Google Scholar
  • For reviews, see:
  • 2k Peters R. Jautze S. Synthesis  2010,  365 
  • 2l Hiemstra H. Marcelli T. Synthesis  2010,  1229 
  • 2m Huang Y. Domling A. Synthesis  2010,  2859 
  • 3a Felpin FX. Lebreton J. Eur. J. Org. Chem.  2003,  3693 
  • 3b Couty F. Amino Acids  1999,  16:  297 
    Search in Google Scholar
  • 3c Buffat MGP. Tetrahedron  2004,  60:  1701 ; and references therein
    Search in Google Scholar
  • 3d Speckamp WN. Hiemstra H. Tetrahedron  1985,  41:  4367 
    Search in Google Scholar
  • 3e Shipman M. Clarkson GJ. Wynne E. Tetrahedron Lett.  2008,  49:  250 
    Search in Google Scholar
  • 3f Bailey PD. Millwood PA. Smith PD. Chem. Commun.  1998,  633 
  • 3g Cortez GA. Schrock RR. Hoveyda AH. Angew. Chem. Int. Ed.  2007,  46:  4534 
    Search in Google Scholar
  • 3h Watson PS. Jiang B. Scott B. Org. Lett.  2000,  2:  3679 
    Search in Google Scholar
  • 4a Carballo RM. Ramirez MA. Rodriguez ML. Martin VS. Padron JI. Org. Lett.  2006,  8:  3837 
    Search in Google Scholar
  • 4b Kishi Y. Nagura H. Inagi S. Fuchigami T. Chem. Commun.  2008,  3876 
  • 5a Yadav JS. Reddy BVS. Chaya DN. Kumar GGKSN. Naresh P. Aravind S. Kunwar AC. Madavi C. Tetrahedron Lett.  2008,  49:  3330 
    Search in Google Scholar
  • 5b Yadav JS. Reddy BVS. Chaya DN. Kumar GGKSN. Naresh P. Jagadeesh B. Tetrahedron Lett.  2009,  50:  1799 
    Search in Google Scholar
  • 6a Guerrier L. Royer J. Grierson DS. Husson H. J. Am. Chem. Soc.  1983,  105:  7754 
    Search in Google Scholar
  • 6b Moody CJ. Lightfoot AP. Gallagher PT. J. Org. Chem.  1997,  62:  746 
    Search in Google Scholar
  • 6c Klegraf E. Follmann M. Schollmeyer D. Kunz H. Eur. J. Org. Chem.  2004,  3346 
  • 6d Airiau E. Girard N. Pizzeti M. Salvadori J. Taddei M. Mann A. J. Org. Chem.  2010,  75:  8670 
    Search in Google Scholar
  • 7a Chattopadhyay SK. Biswas T. Biswas T. Tetrahedron Lett.  2008,  49:  1365 
    Search in Google Scholar
  • 7b Vink MKS. Schortinghuis CA. Luten J. van Maarseveen JH. Schoemaker HE. Hiemstra H. Rutjes FPJT. J. Org. Chem.  2002,  67:  7869 
    Search in Google Scholar
  • 7c Rutjes FPJT. Veerman JJN. Meester WJN. Hiemstra H. Schoemaker HE. Eur. J. Org. Chem.  1999,  1127 
  • 8a Lemire A. Charette AB. J. Org. Chem.  2010,  75:  2077 
    Search in Google Scholar
  • 8b Fadel A. Lahrache N. J. Org. Chem.  2007,  72:  1780 
    Search in Google Scholar
  • 9a Sibi MP. Christensen JW. J. Org. Chem.  1999,  64:  6434 
    Search in Google Scholar
  • 9b Wilson SR. Sawicki RA. J. Org. Chem.  1979,  44:  330 
    Search in Google Scholar
  • 9c Hart DJ. Tsai Y.-M. Choi J.-K. Burnett DA. J. Am. Chem. Soc.  1984,  106:  8201 
    Search in Google Scholar
  • 10 For the data of compound E, see: Takahata H. Banba Y. Ouchi H. Nemoto H. Kato A. Adachi I. J. Org. Chem.  2003,  68:  3603 
    Search in Google Scholar
  • 11a Lebrun S. Couture A. Deniau E. Grandclaudon P. Tetrahedron: Asymmetry  2008,  19:  1245 
    Search in Google Scholar
  • 11b Vetter J. Food Chem. Toxicol.  2004,  42:  1373 
    Search in Google Scholar
  • 11c Reynolds TR. Phytochemistry  2005,  66:  1399 
    Search in Google Scholar
  • 12 Davis FA. Song M. Augustine A. J. Org. Chem.  2006,  71:  2779 
    Search in Google Scholar
  • 13 Lu Z.-H. Zhou W.-S. Tetrahedron  1993,  49:  4659 
    Search in Google Scholar
  • 14a Lamarre D. Croteau G. Bourgon L. Thibeault D. Wardrop E. Clouette C. Vaillancourt M. Cohen E. Pargellis C. Yoakim C. Anderson P. Antimicrob. Agents Chemother.  1997,  41:  965 
    Search in Google Scholar
  • 14b Anderson PC, Soucy F, Yoakim C, Lavallee P, and Beaulieu PL. inventors; US Patent 5 614  533.  ; Chem. Abstr. 1997, 2131185
  • 14c Wu WJ. Raleigh DP. J. Org. Chem.  1998,  63:  6689 
    Search in Google Scholar
  • 14d Cowell SM. Lee YS. Cain JP. Hurby VJ. Curr. Med. Chem.  2004,  11:  2785 
    Search in Google Scholar
  • 15a Komoto T, Yano K, Ono J, Okawa J, and Nakajima T. inventors; JP Patent  61035788. 
  • 15b Takemoto Y. Ueda S. Takeuchi J. Nakmoto T. Iwata C. Tetrahedron Lett.  1994,  35:  8821 
    Search in Google Scholar
  • 16a Beaulieu PL. Lavallee P. Abraham A. Anderson PC. Boucher C. Bousquet Y. Duceppe J. Gillard J. Gorys V. Grand-Maitre C. Grenier L. Guindon Y. Guse I. Plamondon L. Soucy F. Valois S. Wernic D. Yoakim C. J. Org. Chem.  1997,  62:  3440 
    Search in Google Scholar
  • 16b Anderson PC, Souey F, Yoakim C, Lavallee P, and Beaulieu PL. inventors; US Patent  5.545.640. 
  • 17a Liang N. Datta A. J. Org. Chem.  2005,  70:  10182 
    Search in Google Scholar
  • 17b Nair LG. Saksena A. Lovey R. Sannigrahi M. Wong J. Kong J. Fu X. Girijavallabhan V. J. Org. Chem.  2010,  75:  1285 
    Search in Google Scholar
  • 17c Confalonieri G. Marrotta E. Rama F. Righi P. Rosini G. Serra R. Venturelli F. Tetrahedron  1994,  50:  3235 
    Search in Google Scholar
  • 18a Morrison RI. Biochem. J.  1953,  53:  474 
    Search in Google Scholar
  • 18b Pastuszak I. Molyneux RJ. James LF. Elbein AD. Biochemistry  1990,  29:  1886 
    Search in Google Scholar
  • 19 Portoghese PS. Pazdernik TL. Kuhn WL. Hite G. Shafiee A. J. Med. Chem.  1968,  11:  12 
    Search in Google Scholar
  • 20a Tanaka H. Kuroda A. Marusawa H. Hatanaka H. Kino T. Goto T. Hashimoto M. Taga T. J. Am. Chem. Soc.  1987,  109:  5031 
    Search in Google Scholar
  • 20b Ireland RE. Gleason JL. Gegnas LD. Highsmith TK. J. Org. Chem.  1996,  61:  6856 
    Search in Google Scholar
  • 21a Swindells DCN. White PS. Findlay JA. Can. J. Chem.  1978,  56:  2491 
    Search in Google Scholar
  • 21b Smith AB. Condon SM. McCauley JA. Leazer JL. Jr. Leahy JW. Maleczka RE. Jr. J. Am. Chem. Soc.  1997,  119:  962 
    Search in Google Scholar
  • 22 Pastuszak I. Molyneux RJ. James LF. Elbein AD. Biochemistry  1990,  29:  1886 
    Search in Google Scholar
  • 23 Skiles JW. Giannousis PP. Fales KR. Bioorg. Med. Chem. Lett.  1996,  6:  963 
    Search in Google Scholar
  • 24a Michael JP. Nat. Prod. Rep.  2005,  22:  603 
    Search in Google Scholar
  • 24b Erspamer V. Melchiorri P. Trends Pharmacol. Sci.  1980,  1:  391 
    Search in Google Scholar
  • 24c Aronstam RS. Daly JW. Spande TF. Narayanan TK. Albuquerque EX. Neurochem. Res.  1986,  11:  1227 
    Search in Google Scholar
  • 25a Xiaotao P. Dawei M. J. Org. Chem.  2003,  68:  4400 
    Search in Google Scholar
  • 25b Padwa A. Harris JM. J. Org. Chem.  2003,  68:  4371 
    Search in Google Scholar
  • 26 Baskaran S. Kumar GDK. J. Org. Chem.  2005,  70:  4520 
    Search in Google Scholar