N-tert -Butanesulfinyl Imines in Alkaloid Synthesis: Stereoselective Synthesis of (R)-Coniine and Formal Synthesis of (S)-Coniceine 1

Synthesis

Volumn , Issue 15, 2011, Pages 2478-2482

  Damodar, Kongara ^a   Lingaiah, Maram ^a   Bhunia, Nisith ^a   Das, Biswanath ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

alkaloids; piperidines; stereoselective synthesis

Indexed keywords

ALKALOIDS; DIASTEREOSELECTIVE; FORMAL SYNTHESIS; PIPERIDINES; STEREOSELECTIVE SYNTHESIS;

METABOLITES; NITROGEN COMPOUNDS; STEREOCHEMISTRY;

STEREOSELECTIVITY;

ALKALOID; CASTANOSPERMINE; CONIINE; DELTA CONICEINE; IMINE; N TERT BUTANESULFINYL IMINE DERIVATIVE; PIPECOLIC ACID; SWAINSONINE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHEMICAL STRUCTURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 79960839628     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260117     Document Type: Article

References (50)

1. Strunz G M., Findlay J A., In The Alkaloids: Chemistry and Pharmacology Vol. 26 Brossi A Academic Press San Diego 1986 89
2. Fodor G B., Colasanti B, In Alkaloids: Chemical and Biological Perspectives Vol. 3 Pelletier S W. Wiley New York 1986 1
3. For reviews on piperidine alkaloids, see:, Plunkett A O., Nat. Prod. Rep. 1994 11 581
4. Hammann P, In Organic Synthesis Highlights II Waldmann H VCH Weinheim 1995 323
5. Schneider M J., In Alkaloids: Chemical and Biological Perspectives Vol. 10 Pelletier S W. Wiley New York 1996 155
6. OHagan D, Nat. Prod. Rep. 2000 17 435
7. Bailey P D., Millwood P A., Smith P D., Chem. Commun. 1998 633
8. For reviews on indolizidine alkaloids, see:, Takahata H, Momose T, In The Alkaloids: Chemistry and Pharmacology Vol. 44 Cordell G A. Academic Press San Diego 1993 189
9. Michael J P., Nat. Prod. Rep. 2008 25 139
10. Michael J P., Nat. Prod. Rep. 2007 24 191
11. Daly J W., Garraffo H M., Spande T F., J. Nat. Prod. 2005 68 1556
12. Daly J W., J. Med. Chem. 2003 46 445
13. Daly J W., Garraffo H M., Spande T F., In Alkaloids: Chemical and Biological Perspectives Vol. 13 Pelletier S W. Pergamon Oxford 1999 1
14. Reding M T., Buchwald S L., J. Org. Chem. 1998 63 6344
15. Wilkinson T J., Stehle N W., Beak P, Org. Lett. 2000 2 155
16. Nukui S, Sodeoka M, Shibasaki M, Tetrahedron Lett. 1993 34 4965
17. Sato Y, Nukui S, Sodeoka M, Shibasaki M, Tetrahedron 1994 50 371
18. Takahata H, Kubota M, Takahashi S, Momose T, Tetrahedron: Asymmetry 1996 7 3047
19. Panchgalle S P., Bidwai H B., Chavan S P., Kalkote U R., Tetrahedron: Asymmetry 2010 21 2399
20. Coldham I, Leonori D, J. Org. Chem. 2010 75 4069
21. Enders D, Tiebes J, Liebigs Ann. Chem. 1993 173
22. Oppolzer W, Pure Appl. Chem. 1994 66 2127
23. Munchhof M J., Meyers A I., J. Org. Chem. 1995 60 7084
24. Kim Y, Choi J, Tetrahedron Lett. 1996 37 5543
25. Moody C, Lightfoot A, Gallagher P, J. Org. Chem. 1997 62 746
26. Pandey G, Das P, Tetrahedron Lett. 1997 38 9073
27. Yamazaki N, Kibayashi C, Tetrahedron Lett. 1997 38 4623
28. Katritzky A, Qiu G, Yang B, Steel P, J. Org. Chem. 1998 63 6699
29. Takahata H, Kubota M, Ikota N, J. Org. Chem. 1999 64 8594
30. Eskici M, Gallagher T, Synlett 2000 1360
31. Bois F, Gardette D, Gramain J C., Tetrahedron Lett. 2000 41 8769
32. Pachamuthu K, Vankar Y D., J. Organomet. Chem. 2001 624 359
33. Davis S B., McKervey M A., Tetrahedron Lett. 1999 40 1229
34. Yoda H, Katoh H, Ujihara Y, Takabe K, Tetrahedron Lett. 2001 42 2509
35. Hjelmgaard T, Gardette D, Tanner D, Aitken D J., Tetrahedron: Asymmetry 2007 18 671
36. Costa A, Naejera C, Sansano J M., Tetrahedron: Asymmetry 2001 12 205
37. Park S H., Kang H J., Ko S, Park S, Chang S, Tetrahedron: Asymmetry 2001 12 2621
38. Groaning M D., Meyers A I., Chem. Commun. 2000 1027
39. Serino C, Stehle N, Park Y S., Florio S, Beak P, J. Org. Chem. 1999 64 1160
40. Sánchez-Sancho F, Herradón B, Tetrahedron: Asymmetry 1998 9 1951
41. Pilli R A., deFátimaAlves C, Böckelmann M A., Mascarentas Y P., Nery J G., Vencato I, Tetrahedron Lett. 1999 40 2891
42. Robak M T., Herbage M A., Ellman J A., Chem. Rev. 2010 110 3600
43. Das B, Laxminarayana K, Krishnaiah M, Kumar D N., Bioorg. Med. Chem. Lett. 2009 19 6396
44. Das B, Suneel K, Satyalakshmi G, Kumar D N., Tetrahedron: Asymmetry 2009 20 1536
45. Das B, Kumar D N., Tetrahedron Lett. 2010 51 6011
46. Cogan D A., Ellman J A., J. Am. Chem. Soc. 1999 121 268
47. Liu G, Cogan D A., Owens T D., Tang T P., Ellman J A., J. Org. Chem. 1999 64 1278
48. Foubelo F, Yus M, Tetrahedron: Asymmetry 2004 15 3823
49. Wang B, Liu R.-H, Eur. J. Org. Chem. 2009 2845
50. Plechiers M, Hootele C, Tetrahedron Lett. 1993 34 7569