Versatile Synthetic Approaches Towards Aza-analogues of Illudin and Ptaquilosin Sesquiterpenes

Synlett

Volumn 1997, Issue 1, 1997, Pages 25-26

  Anichini, Beatrice ^a   Goti, Andrea ^a   Brandi, Alberto ^a   Kozhushkov, Sergei I ^b   De Meijere, Armin ^b  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002303024     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-684     Document Type: Article

References (26)

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2. (b) Anchel, M.; Hervey, A.; Robbins, W. J. Proc. Nat. Acad. Sci. U. S. A. 1952, 38, 927.
3. (c) McMorris, T. C.; Anchel, M. J. Am. Chem. Soc. 1965, 87, 1594.
4. (d) McMorris, T. C.; Kelner, M. J.; Chadha, R. K.; Siegel, J. S.; Moon, S.; Moya, M. M. Tetrahedron 1989, 45, 5433.
5. (a) Niwa, H.; Ojika, M.; Wakamatzu, K.; Yamada, K.; Ohba, S.; Saito, Y.; Hirono, I.; Matsushita, K. Tetrahedron Lett. 1983, 24, 5371.
6. (b) Ohba, S.; Saito, Y.; Hirono, I.; Niwa, H.; Ojika, M.; Wakamatzu, K.; Yamada, K. Acta Crystallogr., Sect. C 1984, 40, 1877.
7. (c) Ojika, M.; Wakamatzu, K.; Niwa, H.; Yamada, K. Tetrahedron 1987, 43, 5261.
8. Illudins: (a) Kelner, M. J.; McMorris, T.; Beck, W. T.; Zamora, J. M.; Taetle, R. Cancer Research 1987, 47, 3186. (b) Kelner, M. J.; McMorris, Taetle, R. J. Natl. Cancer Inst. 1990, 82, 1562. (c) McMorris, T. C.; Kelner, M. J.; Wang, W.; Moon, S.; Taetle, R. Chem. Res. Toxicol. 1990, 3, 574. (d) McMorris, T. C.; Kelner, M. J.; Wang, W.; Estes, L. A.; Montoya, M. A.; Taetle, R. J. Org. Chem. 1992, 57, 6876.
9. Illudins: (a) Kelner, M. J.; McMorris, T.; Beck, W. T.; Zamora, J. M.; Taetle, R. Cancer Research 1987, 47, 3186. (b) Kelner, M. J.; McMorris, Taetle, R. J. Natl. Cancer Inst. 1990, 82, 1562. (c) McMorris, T. C.; Kelner, M. J.; Wang, W.; Moon, S.; Taetle, R. Chem. Res. Toxicol. 1990, 3, 574. (d) McMorris, T. C.; Kelner, M. J.; Wang, W.; Estes, L. A.; Montoya, M. A.; Taetle, R. J. Org. Chem. 1992, 57, 6876.
10. Illudins: (a) Kelner, M. J.; McMorris, T.; Beck, W. T.; Zamora, J. M.; Taetle, R. Cancer Research 1987, 47, 3186. (b) Kelner, M. J.; McMorris, Taetle, R. J. Natl. Cancer Inst. 1990, 82, 1562. (c) McMorris, T. C.; Kelner, M. J.; Wang, W.; Moon, S.; Taetle, R. Chem. Res. Toxicol. 1990, 3, 574. (d) McMorris, T. C.; Kelner, M. J.; Wang, W.; Estes, L. A.; Montoya, M. A.; Taetle, R. J. Org. Chem. 1992, 57, 6876.
11. Illudins: (a) Kelner, M. J.; McMorris, T.; Beck, W. T.; Zamora, J. M.; Taetle, R. Cancer Research 1987, 47, 3186. (b) Kelner, M. J.; McMorris, Taetle, R. J. Natl. Cancer Inst. 1990, 82, 1562. (c) McMorris, T. C.; Kelner, M. J.; Wang, W.; Moon, S.; Taetle, R. Chem. Res. Toxicol. 1990, 3, 574. (d) McMorris, T. C.; Kelner, M. J.; Wang, W.; Estes, L. A.; Montoya, M. A.; Taetle, R. J. Org. Chem. 1992, 57, 6876.
12. Ptaquiloside: (a) Kushida, T.; Uesugi, M.; Sugiura, Y.; Kigoshi, H.; Tanaka, H.; Hirokawa, J.; Ojika, M.; Yamada, K. J. Am. Chem. Soc. 1994, 116, 479. (b) Kigoshi, H.; Imamura, Y.; Mizuta, K.; Niwa, H.; Yamada, K. J. Am. Chem. Soc. 1993, 115, 3056. (c) Kigoshi, H.; Tanaka, H.; Hirokawa, J.; Mizuta, K.; Yamada, K. Tetrahedron Lett. 1992, 33, 6647.
13. Ptaquiloside: (a) Kushida, T.; Uesugi, M.; Sugiura, Y.; Kigoshi, H.; Tanaka, H.; Hirokawa, J.; Ojika, M.; Yamada, K. J. Am. Chem. Soc. 1994, 116, 479. (b) Kigoshi, H.; Imamura, Y.; Mizuta, K.; Niwa, H.; Yamada, K. J. Am. Chem. Soc. 1993, 115, 3056. (c) Kigoshi, H.; Tanaka, H.; Hirokawa, J.; Mizuta, K.; Yamada, K. Tetrahedron Lett. 1992, 33, 6647.
14. Ptaquiloside: (a) Kushida, T.; Uesugi, M.; Sugiura, Y.; Kigoshi, H.; Tanaka, H.; Hirokawa, J.; Ojika, M.; Yamada, K. J. Am. Chem. Soc. 1994, 116, 479. (b) Kigoshi, H.; Imamura, Y.; Mizuta, K.; Niwa, H.; Yamada, K. J. Am. Chem. Soc. 1993, 115, 3056. (c) Kigoshi, H.; Tanaka, H.; Hirokawa, J.; Mizuta, K.; Yamada, K. Tetrahedron Lett. 1992, 33, 6647.
15. Brandi, A.; Cordero, F. M.; De Sarlo F.; Goti, A.; Guarna, A. Synlett 1993, 1.
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21. Anichini, B.; Goti, A.; Brandi, A.; Kozhushkov, S. I.; de Meijere, A. J. Chem. Soc., Chem. Commun., submitted.
22. Racemization of nitrone 5 under the reaction conditions has been ruled out by check of the enantiomeric purity of indolizidinone 9 by means of an Europium shift reagent. Moreover, the same equilibration at C-3 of nitrone 6 would lead to diastereomeric products 11 that were not observed.
23. Goti, A.; Brandi, A.; Danza, G.; Guarna, A., Donati, D.; De Sarlo, F. J. Chem. Soc., Perkin Trans. 1 1989, 1253.
24. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339.
25. Citti, L.; Nevischi, S.: personal communication. Results of tests will be reported elsewhere.
26. 2: C, 66.27; H, 8.34; N, 7.73. Found: C, 66.04; H, 8.66; N, 7.83.