Synlett 2015; 26(07): 937-941
DOI: 10.1055/s-0034-1380151
letter
© Georg Thieme Verlag Stuttgart · New York

Bisnucleophilic Substitution as a Synthetic Tool for Ready Access to the Piperidine Alkaloids (+)-Connine, (+)-β-Conhydrine, (+)-8-Ethylnorlobelol, and (–)-Halosaline

Galla Raju
Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India   Email: prkgenius@iict.res.in
,
Kadimi Anitha
Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India   Email: prkgenius@iict.res.in
,
Palakodety Radha Krishna*
Organic & Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India   Email: prkgenius@iict.res.in
› Author Affiliations
Further Information

Publication History

Received: 19 November 2014

Accepted after revision: 14 January 2015

Publication Date:
19 February 2015 (online)


Abstract

Herein we report the stereoselective total synthesis of (+)-connine, (+)-β-conhydrine, (+)-8-ethylnorlobelol, and (–)-halosaline via bisnucleophilic substitution with benzylamine as the key step.

Supporting Information

 
  • References and Notes

    • 1a Jones TH, Blum MS In Alkaloids: Chemical and Biological Perspectives . Vol. 1. Pelletier SW. Chap. 2 Wiley; New York: 1983: 33-84
    • 1b Fodor GB, Colasanti B In Alkaloids: Chemical and Biological Perspectives . Vol. 3. Pelletier SW. Chap. 1 Wiley; New York: 1985: 1-90
    • 1c Schneider MJ In Alkaloids: Chemical and Biological Perspectives . Vol. 10. Pelletier SW. Chap. 3 Wiley; New York: 1996: 155-315
    • 1d Strunz GM, Findlay JA In The Alkaloids . Vol. 26. Brossi A. Chap. 3 Academic Press; London: 1985: 89-183
    • 1e Numata A, Ibuka I In The Alkaloids . Vol. 31. Brossi A. Academic; New York: 1987: 193-315
    • 1f Angle RS, Breitenbucher JG. Stereoselective Synthesis . In Studies in Natural Products Chemistry . Vol. 16, Part J. Atta-ur-Rahman, Ed. Elsevier; Amsterdam: 1995: 453-502
    • 2a Radha Krishna P, Sreesailam A. Tetrahedron Lett. 2007; 48: 6924
    • 2b Radha Krishna P, Dayaker G. Tetrahedron Lett. 2007; 48: 7279
    • 2c Radha Krishna P, Reddy BK. Tetrahedron: Asymmetry 2013; 24: 758
    • 2d Radha Krishna P, Lopinti K. Synlett 2007; 1741
    • 3a Davies SG, Iwamoto K, Smethurst CA. P, Smith AD, Rodriguez-Solla H. Synlett 2002; 1146
    • 3b Bates RW, Sa-Ei K. Tetrahedron 2002; 58: 5957
    • 3c Chippindale AM, Davies SG, Iwamoto K, Parkin RM, Smethurst CA. P, Smith AD, Rodriguez-Solla H. Tetrahedron 2003; 59: 3253
    • 3d Burke AJ, Davies SG, Garner AC, McCarthy TD, Roberts PM, Smith AD, Rodriguez-Solla H, Vickers RJ. Org. Biomol. Chem. 2004; 2: 1387
    • 3e Nomura H, Richards CJ. Org. Lett. 2009; 11: 2892
    • 3f Kondekar NB, Kumar P. Synthesis 2010; 3105
    • 3g Airiau E, Girard N, Pizzeti M, Salvadori J, Taddei M, Mann A. J. Org. Chem. 2010; 75: 8670
    • 3h Davies SG, Hughes DG, Price PD, Roberts PM, Russel AJ, Smith AD, Thomson JE, Williams OM. H. Synlett 2010; 567
    • 3i Satyalakshmi G, Suneel K, Shinde DB, Das B. Tetrahedron: Asymmetry 2011; 22: 1000
    • 3j Beng TK, Gawley RE. J. Am. Chem. Soc. 2010; 132: 12216
    • 4a Ratovelomanana-Vidal V, Royer J, Husson HP. Tetrahedron Lett. 1985; 26: 3803
    • 4b Comins DL, Williams AL. Tetrahedron Lett. 2000; 41: 2839
    • 4c Lebrun S, Couture A, Deniau E, Grandclaudon P. Tetrahedron: Asymmetry 2008; 19: 1245
    • 4d Deshmukh SC, Roy A, Talukdar P. Org. Biomol. Chem. 2012; 10: 7536
    • 4e Bhat C, Tilve SG. Tetrahedron 2013; 69: 10876
    • 4f Kamal A, Vangala SR, Reddy NV. S, Reddy VS. Tetrahedron: Asymmetry 2009; 20: 2589
    • 5a Mill S, Durant A, Hootelk C. Liebigs Ann. 1996; 2083
    • 5b Takahata H, Kubota M, Momose T. Tetrahedron Lett. 1997; 38: 3451
    • 5c Takahata H, Kubota M, Ikota N. J. Org. Chem. 1999; 64: 8594
    • 5d Reddy BV. S, Reddy BP, Reddy PS, Reddy YJ, Yadav JS. Tetrahedron Lett. 2013; 54: 4960
    • 6a Takahata H, Kubota M, Momose T. Tetrahedron Lett. 1997; 38: 3451
    • 6b Stragies R, Blechert S. Tetrahedron 1999; 55: 8179
    • 6c Takahata H, Kubota M, Ikota N. J. Org. Chem. 1999; 64: 8594
    • 6d Kochi T, Tang TP, Ellmann JA. J. Am. Chem. Soc. 2003; 125: 11276
    • 6e Lesma G, Crippa S, Danieli B, Passarella D, Sacchetti A, Silvani A, Virdis A. Tetrahedron 2004; 60: 6437
    • 6f Maio WA, Sinishtaj S, Posner GH. Org. Lett. 2007; 9: 2673
    • 6g Sancibrao P, Karila D, Koulovsky C, Vincent G. J. Org. Chem. 2010; 75: 4333
    • 6h Radha Krishna P, Reddy BK, Srinivas P. Tetrahedron 2012; 68: 841
  • 7 Radha Krishna P, Anitha K, Raju G. Tetrahedron 2013; 69: 1649
  • 8 Radha Krishna P, Nomula R, Ramana DV. Tetrahedron Lett. 2012; 53: 3612
  • 9 Crimmins MT, Powell MT. J. Am. Chem. Soc. 2003; 125: 7592
    • 10a Chavan SP, Harale KR. Tetrahedron Lett. 2012; 53: 4683
    • 10b Nomula R, Raju G, Radha Krishna P. Tetrahedron Lett. 2012; 55: 5976
  • 11 Radha Krishna P, Anitha K. Tetrahedron Lett. 2011; 52: 4546
  • 12 Raju G, Nomula R, Radha Krishna P. Tetrahedron Lett. 2014; 55: 6655
  • 13 Mallick A, Kumari N, Roy R, Palanivel A, Vankar YD. Eur. J. Org. Chem. 2014; 5557
  • 14 Ladenberg A, Adam G. Ber. Dtsch. Chem. Ges. 1891; 24: 1671
    • 15a Wertheim T. Liebigs Ann. Chem. 1856; 100: 328
    • 15b Spath E, Adler E. Monatsh. Chem. 1933; 63: 127
    • 16a Wieland H, Koschara W, Dane E, Renz J, Schwarze W. Liebigs Ann. Chem. 1939; 540: 103
    • 16b Mill S, Durant A, Hootele C. Liebigs Ann. 1996; 2083
  • 17 Michel KH, Sandberg F, Haglid F, Norin T. Acta Pharm. Suec. 1967; 4: 97
  • 18 Please see Supporting Information for data and NMR spectra.