Stereoselective synthesis of dendrobate alkaloid (+)-241D and its C-4 epimer

Tetrahedron Letters

Volumn 51, Issue 7, 2010, Pages 1114-1116

  Sateesh Chandra Kumar, R ^a   Venkateswar Reddy, G ^a   Shankaraiah, G ^a   Suresh Babu, K ^a   Madhusudana Rao, J ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Alkaloid (+) 241D; Piperidine alkaloids; Sharpless asymmetric dihydroxylation; Wacker oxidation

Indexed keywords

ALKALOID DERIVATIVE; MAGNESIUM DERIVATIVE;

ADDITION REACTION; ALLYLATION; ARTICLE; DRUG SYNTHESIS; EPOXIDATION; ONE POT SYNTHESIS; STEREOCHEMISTRY;

EID: 73649101728     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.12.111     Document Type: Article

References (27)

1. Strunz G.M., and Findlay J.A. Pyridine and Piperidine Alkaloids. In: Brossi A. (Ed). The Alkaloids Vol. 26 (1985), Academic Press, New York 89-174
2. Numata A., and Ibuka I. Alkaloids from Ants and Other Insects. In: Brossi A. (Ed). The Alkaloids Vol. 31 (1987), Academic Press, New York 193-315
3. Leclerq S., Thirionet I., Broeders F., Daloze D., Vander Meer R., and Braeckman J.C. Tetrahedron 50 (1994) 8465
4. Daly J.W., Myers C.W., and Whittaker N. Toxicon 25 (1987) 1023
5. Edwards M.W., and Daly J.W. J. Nat. Prod. 51 (1988) 1188
6. Edwards M.W., Garraffo H.M., and Daly J.W. Synthesis (1994) 1167
7. Daly J.W., Nishizawa Y., Edwards M.W., Waters J.A., and Aaronstam R.S. Neurochem. Res. 16 (1991) 489
8. Previous asymmetric synthesis of 1 and its C-4 epimer 2:. Chenevert R., and Dickmann M. J. Org. Chem. 61 (1996) 3332
9. Ciblat S., Calinaud P., Canet J.-L., and Troin Y. J. Chem. Soc., Perkin Trans. 1 (2000) 353
10. Ma D., and Sun H. Org. Lett. 2 (2000) 2503
11. Davis F.A., Chao B., and Rao A. Org. Lett. 3 (2001) 3169
12. Monfray J., Gelas-Mialhe Y., Gramain J.-C., and Remuson R. Tetrahedron: Asymmetry 16 (2005) 1025
13. Gnamm C., Krauter C.M., Brodner K., and Helmchen G. Chem. Eur. J. 15 (2009) 2050
14. Previous racemic synthesis: Ref. 4.
15. Girard N., and Hurvois J.-P. Tetrahedron Lett. 48 (2007) 4097
16. Kumar R.S.C., Sreedhar E., Reddy G.V., Babu K.S., and Rao J.M. Tetrahedron: Asymmetry 20 (2009) 1160
17. Sreedhar E., Kumar R.S.C., Reddy G.V., Robinson A., Babu K.S., and Rao J.M. Tetrahedron: Asymmetry 20 (2009) 440
18. Reddy G.V., Kumar R.S.C., Babu K.S., and Rao J.M. Tetrahedron Lett. 50 (2009) 4117
19. Hanawa H., Hashimoto T., and Maruoka K. J. Am. Chem. Soc. 125 (2003) 1708
20. Capaccio C.A.I., and Varela O. Tetrahedron: Asymmetry 11 (2000) 4945
21. Randl S., and Blechert S. J. Org. Chem. 68 (2003) 8879
22. Kolb H.C., Van Nieuwenhze M.S., and Sharpless K.B. Chem. Rev. (1994) 2483
23. The diastereoselectivity was determined by HPLC [YMC silica column, 150 × 4.6 mm, 5 μ, 210 nm, eluent, i-propanol/hexane, 8:92, 10 μL injection volume, flow rate 1 mL/min retention time 9.57 & 11.05 min].
24. Cink R.D., and Forsyth C.J. J. Org. Chem. 60 (1995) 8122
25. Sabitha G., Sudhakar K., Reddy N.M., Kumar M.R., and Yadav J.S. Tetrahedron Lett. 46 (2005) 6567
26. Randl S., and Blechert S. Tetrahedron Lett. 45 (2004) 1167
27. +.