Stereocontrolled preparation of bicyclic alkaloid analogues: an approach towards the kinabalurine skeleton

Tetrahedron

Volumn 65, Issue 39, 2009, Pages 8259-8268

  Kavanagh, Yvonne ^a   O'Brien, Matthew ^a   Evans, Paul ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; INCARVILLINE; KINABALURINE; SKYTANTHINE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; PAUSON KHAND REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 69049112844     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.07.060     Document Type: Article

References (43)

1. Kam T.-S., Yoganathan K., and Wei C. J. Nat. Prod. 60 (1997) 673-676
2. Chi Y.M., Yan W.M., Chen D.C., Noguchi H., Iitaka Y., and Sankawa U. Phytochemistry 31 (1992) 2930-2932
3. Ichikawa M., Takahashi M., Aoyagi S., and Kibayashi C. J. Am. Chem. Soc. 126 (2004) 16553-16558
4. Ichikawa M., Aoyagi S., and Kibayashi C. Tetrahedron Lett. 46 (2005) 2327-2329
5. Ockey D.A., Lewis M.A., and Schore N.E. Tetrahedron 59 (2003) 5377-5381 and references therein
6. Costantino L., Lins A.P., Barlocco D., Celotti F., El-Abady S.A., Brunetti T., Maggi R., and Antolini L. Pharmazie 58 (2003) 140-142
7. Ernst M., and Helmchen G. Synthesis (2002) 1953-1955 and references therein
8. Robert N., Hoarau C., and Marsais F. Tetrahedron 63 (2007) 3702-3706
9. Buffat M.G.P. Tetrahedron 60 (2004) 1701-1729
10. Watson P.S., Jiang B., and Scott B. Org. Lett. 2 (2000) 3679-3681 a substructure search for the piperidine ring in the MDL drug data report indicated 12,000 discrete piperidines entries for compounds involved in both preclinical and clinical studies for the period 1988-1998
11. Magnus P., and Principe L.M. Tetrahedron Lett. 26 (1985) 4851-4854
12. Magnus P., Exon C., and Albaugh-Robertson P. Tetrahedron 41 (1985) 5861-5869
13. Magnus P., Principe L.M., and Slater M.J. J. Org. Chem. 52 (1987) 1483-1486
14. Breczinski P.M., Stumpf A., Hope H., Krafft M.E., Casalnuovo J.A., and Schore N.E. Tetrahedron 55 (1999) 6797-6812
15. Yoo S.E., and Lee S.H. J. Org. Chem. 59 (1994) 6968-6972
16. For a related example in which an allylic methyl group controls the axial stereochemistry of a Vollhardt cyclisation see:. Stará I.G., Alexandrová Z., Teplý F., Sehnal P., Starý I., Šaman D., Budešínsky M., and Cvačka J. Org. Lett. 7 (2005) 2547-2550
17. For recent reviews, see:
18. Brummond K.M., and Kent J.L. Tetrahedron 56 (2000) 3263-3283
19. Gibson S.E., and Mainolfi N. Angew. Chem., Int. Ed. 44 (2005) 3022-3037
20. Evans P., and Kavanagh Y. In: Kaufman T.S., and Larghi E.L. (Eds). Modern Approaches to the Synthesis of O- and N-Heterocycles Vol. 2 (2007), Research Signpost, Kerala, India 33-78
21. Honda T., and Kaneda K. J. Org. Chem. 72 (2007) 6541-6547
22. Kaneda K., and Honda T. Tetrahedron 64 (2008) 11589-11593
23. Trost B.M., Machacek M.R., and Faulk B.D. J. Am. Chem. Soc. 128 (2006) 6745-6754
24. Shambayti S., Crowe W.E., and Schreiber S.L. Tetrahedron Lett. 31 (1990) 5289-5292
25. Jeong N., Chung Y.K., Lee B.Y., Lee S.H., and Yoo S.-E. Synlett (1991) 204-206
26. 3S: Unit cell parameters: a 5.5026(5); b 9.1774(8); c 16.7670(16); β 96.814(2); space group P21.
27. Flack H.D., and Bernardinelli G. Acta Crystallogr. A55 (1999) 908-915
28. Adrio J., Rodríguez Rivero M., and Carretero J.C. Angew. Chem., Int. Ed. 39 (2000) 2906-2908
29. Adrio J., Rodríguez Rivero M., and Carretero J.C. Synlett (2005) 26-41
30. Boutagy J., and Thomas R. Chem. Rev. 74 (1974) 87-99
31. Evans P., Johnson P., and Taylor R.J.K. Eur. J. Org. Chem. (2006) 1740-1754
32. Günter M., and Gais H.-J. J. Org. Chem. 68 (2003) 8037-8041
33. For a recent exo-selective intramolecular PKR of a vinyl sulfone see:. Krafft M.E., Kyne G.M., Hirosawa C., Schmidt P., Abboud K.A., and L'Helias N. Tetrahedron 62 (2006) 11782-11792
34. Tanaka K., Taniguchi T., and Ogasawara K. Tetrahedron Lett. 42 (2001) 1049-1052
35. Gemal A.L., and Luche J.-L. J. Am. Chem. Soc. 103 (1981) 5454-5459
36. Hoveyda A.H., Evans D.A., and Fu G.C. Chem. Rev. 93 (1993) 1307-1370
37. Brown J.M. Angew. Chem., Int. Ed. Engl. 26 (1987) 190-203
38. Crabtree R.H., and Davis M.W. J. Org. Chem. 51 (1986) 2655-2661
39. Stork G., and Kahne D.E. J. Am. Chem. Soc. 105 (1983) 1072-1073
40. Kavanagh Y., Chaney C.M., Muldoon J., and Evans P. J. Org. Chem. 73 (2008) 8601-8604
41. House H.O., Giese R.W., Kronberger K., Kaplan J.P., and Simeone J.F. J. Am. Chem. Soc. 92 (1970) 2800-2810
42. van Zijl A.W., López F., Minnaard A.J., and Feringa B.L. J. Org. Chem. 72 (2007) 2558-2563
43. Blumenkopf T.A. Synth. Commun. 16 (1986) 139-147