Regiocontrol in the rhodium (II) catalysed reactions of 1,2,3,4-tetrahydro-1-naphthyl diazomethyl ketones: Potential applications to the synthesis of galbulimima alkaloids

Tetrahedron Letters

Volumn 38, Issue 32, 1997, Pages 5709-5712

  Mander, Lewis N ^a   Wells, Adam P ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

GALBULIMIMA;

EID: 0030838717     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01252-5     Document Type: Article

References (24)

1. Ritchie, E.; Taylor, W.C. in The Alkaloids, Manske, R.H.F. Ed.; Academic Press; New York, 1967; Vol 9, pp 529-613; 1971; Vol. 13, pp 227-271.
2. Ritchie, E.; Taylor, W.C. in The Alkaloids, Manske, R.H.F. Ed.; Academic Press; New York, 1967; Vol 9, pp 529-613; 1971; Vol. 13, pp 227-271.
3. See references cited in refs 3(a) and 3(b).
4. (a) Chackalamannil, S.; Davies, R.J.; Asberom, T.; Doller, D.; Leone, D. J. Am. Chem. Soc. 1996, 118, 9812.
5. (b) Hart, D.J.; Wu, W.-L.; Kozikowski, A.P. J. Am. Chem. Soc. 1995, 117, 9369.
6. See also: (a) Baldwin, J.E.; Chesworth, R.; Parker, J.S.; Russell, A.T. Tetrahedron Lett. 1995, 36, 9551.
7. (b) Baecke, G.D.; De Clerq, P. Tetrahedron Lett. 1995, 36, 7515.
8. Mander, L.N.; Ritchie, E.; Taylor, W.C. Aust. J. Chem. 1967, 20, 981.
9. Mander, L.N.; Prager, R.H.; Ritchie, E.; Taylor, W.C. Aust. J. Chem. 1967, 20, 1705.
10. Mander, L.N.; Prager, R.H.; Rasmussen, M.; Ritchie, E; Taylor, W.C. Aust. J. Chem. 1967, 20, 1473.
11. 1
12. D. H. Rogers; D.H. Morris, J.C.; Roden, F.S.; Frey, B.; King, G.R.; Russkamp, F.-W.; Bell, R.A.; Mander, L.N. Pure Appl Chem. 1996, 68, 515.
13. Padwa, A.; Austin, D.J.; Price, A.T.; Semones, M.A.; Doyle M.P.; Protopopova, N.M.; Winchester W.R.; Tran, A. J. Am. Chem. Soc. 1993, 115, 8669.
14. Kumar, A.; Singh, R.; Mandai, A. Syn . Commun. 1982, 12, 613.
15. Maiti, S.B.; Chaudhuri, S.R.R.; Chaterjee, A. Synthesis, 1987, 806.
16. Gassman, P.G.; Schenk, W.N. J. Org. Chem. 1977, 42, 918.
17. 13C NMR δ 23.80, 24.0, 25.02, 25.79, 27.21, 30.67, 44.92, 47.70, 55.08, 67.66, 112.71, 113.41, 125.61, 128.32, 138.59, 157.74, 210.81.
18. Doyle, M.P. Chem. Rev. 1986, 86, 919.
19. Padwa, A.; Austin, D.J.; Hornbuckle, S.F. J. Org. Chem. 1996, 61, 63.
20. Padwa, A.; Austin, D.J. Angew. Chem., Int. Ed. Eng. 1994, 33, 1797.
21. Ye, T.; McKervey, M.A. Chem. Rev. 1994, 94, 1091.
22. Watanabe, N.; Ohtake, Y.; Hashimoto, S.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 1491.
23. Ahsan, M.Q.; Bernal, I.; Bear, J.L. Inorg. Chem. 1986, 25, 260.
24. Hashimoto, S.; Watanabe, N.; Ikegami, S. J. Chem. Soc. Chem. Commun. 1992, 1508.