Synthesis of clionamine B, an autophagy stimulating aminosteroid isolated from the sponge Cliona celata

Organic Letters

Volumn 15, Issue 15, 2013, Pages 3918-3921

  Forestieri, Roberto ^a   Donohue, Elizabeth ^a   Balgi, Aruna ^a   Roberge, Michel ^a   Andersen, Raymond J ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CLIONAMINE B; STEROID;

ANIMAL; ARTICLE; AUTOPHAGY; BREAST TUMOR; CELL STRAIN MCF 7; CHEMISTRY; DRUG EFFECT; HUMAN; MARINE BIOLOGY; METABOLISM; NUCLEAR MAGNETIC RESONANCE; PATHOLOGY; SPONGE (PORIFERA); STEREOISOMERISM; SYNTHESIS;

ANIMALS; AUTOPHAGY; BREAST NEOPLASMS; HUMANS; MARINE BIOLOGY; MCF-7 CELLS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PORIFERA; STEREOISOMERISM; STEROIDS;

EID: 84881255349     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4016783     Document Type: Article

References (27)

1. Oczypok, E. A.; Oury, T. D.; Chu, C. T. Am. J. Pathol. 2013, 182, 612-622
2. Codogno, P.; Mehrpour, M.; Proikas-Cezanne, T. Nat. Rev. Mol. Cell. Biol. 2012, 13, 7-12
3. Yang, Z.; Klionsky, D. J. Curr. Opin. Cell. Biol. 2010, 22, 124-131
4. Subramani, S.; Malhotra, V. EMBO rep. 2013, 14, 143-151
5. Yordy, B.; Tai, M. C.; Hayashi, K.; Arojo, O.; Iwasaki, A. Intl. Immunol. 2012, 25, 1-10
6. Mostowy, S. Cell. Microbiol. 2013, 15, 395-402
7. Campoy, E.; Colombo, M. I. Biochim. Biophys. Acta 2009, 1793, 1465-1477
8. Songane, M.; Kleinnijenhuis, J.; Netea, M. G.; van Creval, R. Tuberculosis 2012, 92, 388-396
9. Jones, S. A.; Mills, K. H. G.; Harris, J. Immunol. Cell. Biol. 2013, 91, 250-258
10. Rubinsztein, D. C.; Cogogno, P.; Levine, B. Nat. Rev. Drug Discovery 2012, 11, 709-730
11. Floto, R. A.; Sarkar, S.; Perlstein, E. O.; Kampmann, B.; Schreiber, S. L.; Rubinsztein, D. C. Autophagy 2007, 3, 620-622
12. Pallauf, K.; Rimbach, G. Ageing Res. Rev. 2013, 12, 237-252
13. Rubinsztein, D. C.; Gestwicki, J. E.; Murphy, L. O.; Klionsky, D. J. Nat. Rev. Drug Discovery 2007, 6, 304-312
14. Lam, K. K. Y.; Zheng, X.; Forestieri, R.; Balgi, A. D.; Nodwell, M.; Vollett, S.; Anderson, H. J.; Andersen, R. J.; Av-Gay, Y.; Roberge, M. PLoS Pathogens 2012, 8, e10022691
15. Carr, G.; Williams, D. E.; Díaz-Marrero, A. R.; Patrick, B. O.; Bottriell, H.; Balgi, A. D.; Donohue, E.; Roberge, M.; Andersen, R. J. J. Nat. Prod. 2010, 73, 422-427
16. Keyzers, R. A.; Daoust, J.; Davies-Coleman, M. T.; Van Soest, R.; Balgi, A.; Donohue, E.; Roberge, M.; Andersen, R. J. Org. Lett. 2008, 10, 2959-2962
17. Marker, R. E.; Rohrmann, E. J. Am. Chem. Soc. 1940, 62, 518-520
18. Ibid. 898-900.
19. Marker, R. E.; Krueger, J. J. Am. Chem. Soc. 1940, 62, 3349-3350
20. Djerassi, C. Steroids 1992, 57, 631-641
21. Anulewicz-Ostrowska, R.; Jastrzebska, I.; Morzycki, J. W.; Wójcik, J. J. Org. Chem. 2002, 67, 6916-6924
22. Coburn, C. E.; Anderson, D. K.; Swenton, J. S. J. Org. Chem. 1983, 48, 1455-1461
23. Crossland, R. K.; Servis, K. L. J. Org. Chem. 1970, 35, 3195-3196
24. Chiao, W.-B.; Saunders, W. H. J. Org. Chem. 1980, 45, 1319-1320
25. Bolster, M. G.; Jansen, B. J. M.; de Groot, A. Tetrahedron 2001, 57, 5663-5679
26. House, H. O.; Respess, W. L.; Whitesides, G. M. J. Org. Chem. 1966, 31, 3128-3141
27. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897-2904