Tandem intramolecular photocycloaddition-retro-mannich fragmentation as a route to spiro[pyrrolidine-3,3′-oxindoles]. Total synthesis of (±)-coerulescine, (±)-horsfiline, (±)-elacomine, and (±)-6-deoxyelacomine

Journal of Organic Chemistry

Volumn 75, Issue 11, 2010, Pages 3569-3577

  White, James D ^a   Li, Yang ^a   Ihle, David C ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[2 + 2] CYCLOADDITION; ALKYLIDENES; CYCLOBUTANES; DOUBLE BONDS; HYDRIDE REDUCTION; INDOLENINE; ISOBUTYL; MALONATES; OXINDOLES; PHOTOCYCLOADDITION; PYRROLIDINES; RELATIVE ORIENTATION; SIDE-CHAIN; STARTING MATERIALS; STEREO-SELECTIVE; STEREOCENTERS; TOTAL SYNTHESIS; TRYPTAMINES;

BUTANE; SYNTHESIS (CHEMICAL);

CHEMICAL MODIFICATION;

5 METHOXYTRYPTAMINE; 6 DEOXYELACOMINE; ALKALOID DERIVATIVE; BETA CARBOLINE; COERULESCINE; CYCLOBUTANE; ELACOMINE; HORSFILINE; INDOLE DERIVATIVE; MALONIC ACID; OXINDOLE; PYRROLIDINE DERIVATIVE; SPIRO[PYRROLIDINE 3,3' OXINDOLE]; TRYPTAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; CYCLOADDITION; FRAGMENTATION REACTION; MANNICH REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

ANILINE COMPOUNDS; INDOLES; PHOTOCHEMICAL PROCESSES; SPIRO COMPOUNDS;

EID: 77953005317     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1002714     Document Type: Article

References (51)

1. Ho, T.-L. Tactics of Organic Synthesis; Wiley: New York, 1994; pp 138 - 144.
2. White, J. D.; Dillon, M. P.; Butlin, R. J. J. Am. Chem. Soc. 1992, 114, 9673
3. White, J. D.; Kim, J.; Drapela, N. J. Am. Chem. Soc. 2000, 122, 8665
4. De Mayo, P. Acc. Chem. Res. 1971, 4, 41
5. Inter alia: Büchi, G.; Carlson, J. A.; Powell, J. E.; Tietze, L.-F. J. Am. Chem. Soc. 1973, 95, 540
6. Partridge, J. J.; Chadha, N. K.; Uskokovic, M. R. J. Am. Chem. Soc. 1973, 95, 532
7. Oppolzer, W.; Godel, Y. J. Am. Chem. Soc. 1978, 100, 2583
8. Baker, R.; Sims, R. J. Chem. Soc., Perkin Trans. 1 1981, 3087
9. Piers, E.; Abeysekera, B. F.; Herbert, D. J.; Suckling, I. D. Can. J. Chem. 1985, 63, 3418
10. Disanayala, B. W.; Weedon, A. C. Chem. Commun. 1985, 1282
11. Seto, H.; Fujimoto, Y.; Tatsumo, T.; Yoshioka, H. Synth. Commun. 1985, 15, 1217
12. Crimmins, M. T.; Gould, L. D. J. Am. Chem. Soc. 1987, 109, 6199
13. Cantrell, T. S. Tetrahedron 1971, 27, 1227
14. Schell, F. M.; Cook, P. M. J. Org. Chem. 1984, 49, 4067
15. Winkler, J. D.; Muller, C. L.; Scott, R. D. J. Am. Chem. Soc. 1988, 110, 4831
16. Winkler, J. D.; Hershberger, P. M. J. Am. Chem. Soc. 1989, 111, 4852
17. Winkler, J. D.; Scott, R. D.; Williard, P. G. J. Am. Chem. Soc. 1990, 112, 8971
18. Winkler, J. D.; Axten, J. M. J. Am. Chem. Soc. 1998, 120, 6425
19. Swindell, C. S.; Patel, B. P.; DeSolms, S. J.; Springer, J. P. J. Org. Chem. 1987, 52, 2346
20. White, J. D.; Ihle, D. C. Org. Lett. 2006, 8, 1081
21. Anderton, N.; Cockrum, P. A.; Colegate, S. M.; Edgar, J. A.; Flower, K.; Vit, I.; Willing, R. I. Phytochemistry 1998, 45, 437
22. Anderton, N.; Cockrum, P. A.; Colegate, S. M.; Edgar, J. A.; Flower, K.; Gardner, D.; Willing, R. I. Phytochemistry 1999, 51, 153
23. Jossang, A.; Jossang, P.; Hadi, H. A.; Sevenet, T.; Bodo, B. J. Org. Chem. 1991, 56, 6527
24. Slywka, G. W. A.; Locock, R. A. Tetrahedron Lett. 1969, 4635
25. James, M. N. G.; Williams, G. J. B. Can. J. Chem. 1972, 50, 2407
26. Reviews: Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
27. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
28. Cui, C.-B.; Kakeya, J.; Osada, J. Tetrahedron 1996, 52, 12651
29. The first synthesis of 5 appears to have been an adventitious one recorded by Kuehne; Kuehne, M. E.; Roland, D. M.; Hafter, R J. Org. Chem. 1978, 43, 3705 For subsequent syntheses of 5 and/or 6
30. Kuehne, M. E.; Roland, D. M.; Hafter, R. Heterocycles 1994, 38, 725
31. Pellegrini, C.; Strässler, C.; Weber, M.; Borschberg, H.-J. Tetrahedron: Asymmetry 1994, 5, 1979
32. Lakshmaiah, G.; Kawabata, G.; Shang, M.; Fuji, K. J. Org. Chem. 1999, 64, 1699
33. Kumar, U. K. S.; Ila, H.; Junjappa, H. Org. Lett. 2001, 3, 4193
34. Cravotto, G.; Giovenzana, G. B.; Pilati, T.; Sisti, M.; Palmisano, G. J. Org. Chem. 2001, 66, 8447
35. Lizos, D. E.; Murphy, J. A. Org. Biomol. Chem. 2003, 1, 117
36. Chang, M.-Y.; Pai, C.-L.; Kung, Y.-H. Tetrahedron Lett. 2005, 46, 8463
37. Murphy, J. A.; Tripoli, R.; Khan, T. A.; Mali, U. W. Org. Lett. 2005, 7, 3287
38. Trost, B. M.; Brennan, M. K. Org. Lett. 2006, 8, 2027
39. Momose, T.; Tanaka, T.; Yokota, T.; Nagamoto, N.; Yamada, K. Chem. Pharm. Bull. Jpn. 1978, 26, 2224
40. Horspool, W. M., Ed. Synthetic Organic Photochemistry; Plenum Press: New York, 1984; p 492.
41. Boekelheide, V.; Ainsworth, C. J. Am. Chem. Soc. 1950, 72, 2132
42. Whaley, W. M.; Govindachari, T. R. Org. React. 1951, 6, 151
43. Whaley, W. M.; Govindachari, T. R. Org. React. 1951, 6, 74
44. Lawson, W. B.; Withrop, B. J. Org. Chem. 1961, 26, 263
45. van Tamelen, E. E.; Yardley, J. P.; Miyano, M.; Hinshaw, W. B. J. Am. Chem. Soc. 1969, 91, 7333
46. Li, C.; Chan, C.; Heimann, A.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2007, 46, 1444
47. Huffman, J. W.; Garg, S. P.; Cecil, J. H. J. Org. Chem. 1966, 31, 1276
48. Pellegrini, C.; Weber, M.; Borschberg, H.-J. Helv. Chim. Acta 1996, 79, 151
49. Teranishi, K.; Nakatsuka, K.; Goto, T. Synthesis 1994, 1018
50. Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. Tetrahedron 1958, 2, 1
51. Miyake, F.; Yakushijin, K.; Horne, D. A. Org. Lett. 2004, 6, 711