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

Galla Raju; Kadimi Anitha; Palakodety Radha Krishna

doi:10.1055/s-0034-1380151

Synlett, Table of Contents

Synlett 2015; 26(07): 937-941
DOI: 10.1055/s-0034-1380151

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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

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Abstract

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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.

Key words

bisnucleophilic substitution - (+)-connine - (+)-β-conhydrine - (+)-8-ethylnorlobelol - (–)-halosaline - benzylamine

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References

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.

Supplementary Material

Supporting Information