Total synthesis of psammaplysenes A and B, naturally occurring inhibitors of FOXO1a nuclear export

Organic Letters

Volumn 7, Issue 19, 2005, Pages 4091-4094

  Georgiades, Savvas N ^a   Clardy, Jon ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; FORKHEAD TRANSCRIPTION FACTOR; PSAMMAPLYSENE A; PSAMMAPLYSENES B; TYROSINE;

ACTIVE TRANSPORT; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; METABOLISM; SYNTHESIS;

ACTIVE TRANSPORT, CELL NUCLEUS; FORKHEAD TRANSCRIPTION FACTORS; MOLECULAR STRUCTURE; TYROSINE;

EID: 25444454350     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0513286     Document Type: Article

References (30)

1. (a) Vazquez, F.; Sellers, W. R. Biochim. Biophys. Acta 2000, 1470, M21.
2. (b) Kondo, K.; Yao, M.; Kobayashi, K.; Ota, S.; Yoshida, M.; Kaneko, S.; Baba, M.; Sakai, N.; Kishida, T.; Kawakami, S.; Uemura, H.; Nagashima, Y.; Nakatani, Y.; Hosaka, M. Int. J. Cancer 2001, 91, 219.
3. (c) Kong, D.; Suzuki, A.; Zou, T. T.; Sakurada, A.; Kemp, L. W.; Wakatsuki, S.; Yokoyama, T.; Yamakawa, H.; Furukawa, T.; Sato, M.; Ohuchi, N.; Sato, S.; Yin, J.; Wang, S.; Abraham, J. M.; Souza, R. F.; Smolinski, K. N.; Meltzer, S. J.; Horii, A. Nat. Genet. 1997, 17, 143.
4. (d) Wang, S. I.; Puc, J.; Li, J.; Bruce, J. N.; Cairns, P.; Sidranski, D.; Parsons, R. Cancer Res. 1997, 57, 4183.
5. Kau, T. R.; Schroeder, F.; Ramaswamy, S.; Wojciechowski, C. L.; Zhao, J. J.; Roberts, T. M.; Clardy, J.; Sellers, W. R.; Silver, P. A. Cancer Cell 2003, 4, 463.
6. Schroeder, F. C.; Kau, T. R.; Silver, P. A.; Clardy, J. J. Nat. Prod. 2005, 68, 574.
7. Yagi, H.; Matsunaga, S.; Fusetani, N. Tetrahedron 1993, 49, 3749.
8. Piña, I. C.; Gautschi, J. T.; Wang, G. Y. S.; Sanders, M. L.; Schmitz, F. J.; France, D.; Cornell-Kennon, S.; Sambucetti, L. C.; Remiszewski, S. W.; Perez, L. B.; Bair, K. W.; Crews, P. J. Org. Chem. 2003, 68, 3866.
9. Mack, M. M.; Molinski, T. F.; Buck, E. D.; Pessah, I. N. J. Biol. Chem. 1994, 269, 23236.
10. N-Bromo-tert-butylamine was prepared following a published method: Boozer, C. E.; Moncrief, J. W. J. Org. Chem. 1962, 27, 623.
11. For ortho-directed bromination of unsubstituted phenol with N-bromo-tert-butylamine, see: Jpn. Kokai Tokkyo Koho, 09291053, 11 Nov 1997, Heisei.
12. Jeffery, T. Tetrahedron 1996, 52, 10113.
13. Significant shifts downfield for the peaks corresponding to the methyl and methylene protons on carbons directly attached to the nitrogen of 3 suggest that the tertiary amine is protonated; therefore, 3 must be overall a zwitterion given that it was prepared and isolated in nonacidic conditions. Considerable pH-dependent shifts, even for protons which are two carbons away from the nitrogen, are not unusual for such basic systems.
14. (a) Kan, T.; Fukuyama, T. Chem. Commun. 2004, 4, 353.
15. (b) Kan, T.; Fukuyama, T. J. Synth. Org. Chem. Jpn. 2001, 59, 779.
16. For preparation, see the Supporting Information.
17. (a) Fukuyama, T.; Jow, C. K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
18. (b) Fukuyama, T.; Cheung, M.; Jow, C. K.; Hidai, Y.; Kan, T. Tetrahedron Lett. 1997, 38, 5831.
19. Mitsunobu, O. Synthesis 1981, 1, 1.
20. For preparation, see the Supporting Information.
21. 2(dppf). All cases suffered from either unacceptable yields or poor regioselectivity for the p-iodide position vs the o-bromide positions.
22. 3 in different solvents, under various conditions.
23. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
24. (a) Bowles, D. M.; Anthony, J. E. Org. Lett. 2000, 2, 85.
25. (b) Tobe, Y.; Nakagawa, N.; Kishi, J. Y.; Sonoda, M.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. Tetrahedron 2001, 57, 3629.
26. (c) Tobe, Y.; Utsumi, N.; Nagano, A.; Sonoda, M.; Naemura, K. Tetrahedron 2001, 57, 8075.
27. Han, G.; Tamaki, M.; Hruby, V. J. J. Peptide Res. 2001, 58, 338.
28. For a recent review on ynamine and ynamide research, see: Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L. L. Tetrahedron 2001, 57, 7575 and references therein.
29. 3OD, whereas the rest of the peaks remained essentially unaffected.
30. A recent example involved formation of bis-pyrrole adducts upon treatment of alkylthiochloroacetylenes with pyrrole: Sobenina, L. N.; Dyachkova, S. G.; Stepanova, Z. V.; Toryashinova, D. S. D.; Albanov, A. I.; Ushakov, I. A.; Demenev, A. P.; Mikhaleva, A. I.; Trofimov, B. A. Russ. J. Org. Chem. 1999, 35, 916.