Explorations on the total synthesis of (±)-isoschizogamine using an intramolecular 1,4-dipolar cycloaddition strategy

Arkivoc

Volumn 2010, Issue 6, 2010, Pages 7-21

  Padwa, Albert ^a   Bobeck, Drew R ^a   Mmutlane, Edwin M ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

1,4 Dipolar; Aza Claisen; Betaine; Cross conjugated; Cycloaddition; Heteroaromatic; Rearrangement

Indexed keywords

EID: 77953383757     PISSN: 15517012     EISSN: 15517004     Source Type: None    
DOI: 10.3998/ark.5550190.0011.602     Document Type: Article

References (33)

1. Saxton, J. E. In Indoles, Part Four, The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; John Wiley: New York, 1984; Chapter IX, pp 437-486.
2. Renner, U.; Kernweisz, P. Experientia 1963, 19, 244.
3. Hájicek, J.; Taimr, J.; Budesinsky, M. Tetrahedron Lett. 1998, 39, 505.
4. Renner, U.; Fritz, H. Helv. Chim. Acta 1965, 48, 308.
5. Renner, U. Lloydia 1964, 27, 406.
6. Kariba, R. M.; Houghton, P. J.; Yenesew, A. J. Nat. Prod. 2002, 65, 566.
7. (a) Hájíèek, J.; Trojánek, J. Tetrahedron Lett. 1981, 22, 2927.
8. (b) Hájíèek, J.; Trojánek, J. Tetrahedron Lett. 1982, 23, 365.
9. (c) Hájíèek, J.; Trojánek, J. Collect. Czech. Chem. Commun. 1986, 51, 1731.
10. Hubbs, J. L.; Heathcock, C. H. Org. Lett. 1999, 1, 1315.
11. Kompis, I.; Hesse, M.; Schmid, H. Lloydia 1971, 34, 269.
12. (a) Magomedov, N. A. Org. Lett. 2003, 5, 2509.
13. (b) Zhou, J.; Magomedov, N. A. J. Org. Chem. 2007, 72, 3808.
14. Padwa, A.; Flick, A.; Lee, H. I. Org. Lett. 2005, 7, 2925.
15. (a) Ollis, W. D.; Stanforth, S. P.; Ramsden, C. A. Tetrahedron 1985, 41, 2239.
16. (b) Padwa, A.; Coats. S. J.; Semones, M. A. Tetrahedron 1995, 51, 6651.
17. Potts, K. T.; Rochanapruk, T.; Padwa, A.; Coats, S. J.; Hadjiarapoglu, L. J. Org. Chem. 1995, 60, 3795.
18. (a) Kappe, T.; Golser, W.; Hariri, M.; Stadlbauer, W. Chem. Ber. 1979, 112, 1585.
19. (b) Friedrichsen, W.; Kappe, T.; Böttcher, A. Heterocycles 1982, 19, 1083.
20. (a) Kappe, T.; Ziegler, E. Angew. Chem., Int. Ed. Engl. 1974, 13, 491.
21. (b) Hopff, H.; Hegar, G. Helv. Chim. Acta 1961, 44, 2016.
22. Staudinger, H.; Bereza, S. Ber. 1908, 41, 4461.
23. Carbonyl sulfide was identified by trapping in an alcoholic solution of piperidine where it formed the corresponding salt; see: Seibert, W. Angew. Chem. 1959, 71, 194.
24. Lindstrom, U. M.; Somfai, P. Chem Eur. J. 2001, 7, 94.
25. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
26. (b) Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874.
27. Trost, B. M.; Braslau, R. Tetrahedron Lett. 1989, 30, 4657.
28. Paterson, I.; Yeung, K.-S.; Smaill, J. B. Synlett 1993, 774.
29. (a) Kato, S.; Harada, H.; Morie, T. J. J. Chem. Soc., Perkin Trans. 1997, 1, 3219.
30. (b) Nakajima, K.; Tanaka, T.; Meya, M.; Okawa, K. Bull. Chem. Soc. Jpn. 1982, 55, 3237.
31. Vedejs, E.; Klapars, A.; Warner, D. L.; Weiss, A. H. J. Org. Chem. 2001, 66, 7542.
32. Padwa, A.; Harring, S. R.; Hertzog, D. L.; Nadler, W. R. Synthesis, 1994, 993.
33. The senior author regrets that spectral data for compounds 34-43 are not presented. These compounds (i.e. 34-43) were intermediates for an eventual synthesis of ä-lactam 30. Unfortunately, the reason for this omission is that the data were lost during a move of our laboratory from one location to another and inadvertently discarded during a period of my absence. Because the two junior collaborators have since left the group and are working elsewhere, it is not practical for us to repeat this work with our very limited resources. I do regret that this has happened, but do feel as though the chemistry is reliable. If anyone might be interested in preparing lactam 30 in the future, the details are well laid out. Under these circumstances and with the agreement of the Scientific Editor of Arkivoc, the paper is being published with this deficiency. (Editor's comment - Please note that the special circumstances surrounding this matter will not be taken as a precedent for any future relaxation of Arkivoc's requirements for full characterization).