Scalable total synthesis and biological evaluation of haouamine A and its atropisomer

Journal of the American Chemical Society

Volumn 131, Issue 26, 2009, Pages 9172-9173

  Burns, Noah Z ^a   Krylova, Irina N ^b   Hannoush, Rami N ^b   Baran, Phil S ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b GENENTECH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTICANCER ACTIVITIES; AROMATIC RINGS; ATROPISOMER; BIOLOGICAL EVALUATION; CHEMICAL EQUATIONS; CYCLOHEXENONES; DEPROTECTION; MARINE ALKALOIDS; NATURAL PRODUCTS; PLANAR CHIRALITY; TOTAL SYNTHESIS;

AROMATIC COMPOUNDS; STEREOCHEMISTRY;

SYNTHESIS (CHEMICAL);

2 CYCLOHEXENONE; ALKALOID; ATRO HAOUAMINE A; HAOUAMINE A; PHENOL; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DEHYDROGENATION; DRUG MECHANISM; HUMAN; HUMAN CELL; ISOMER; OXIDATION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HUMANS; MALE; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROSTATIC NEOPLASMS; STEREOISOMERISM;

EID: 67649921097     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja903745s     Document Type: Article

References (20)

1. Garrido, L.; Zubía, E.; Ortega, M. J.; Salvá, J. J. Org. Chem. 2003, 68, 293.
2. Belostotskii, A. M. J. Org. Chem. 2008, 73, 5723.
3. For an example of surprising atropisomerism in a natural product, see: Nicolaou, K. C.; Harrison, S. T. Angew. Chem., Int. Ed. 2006, 45, 3256.
4. Racemic: (a) Baran, P. S.; Burns, N. Z. J. Am. Chem. Soc. 2006, 128, 3908.
5. Enantioselective: (b) Burns, N. Z.; Baran, P. S. Angew. Chem., Int. Ed. 2008, 47, 205.
6. For model studies, see: (a) Smith, N. D.; Hayashida, J.; Rawal, V. H. Org. Lett. 2005, 7, 4309.
7. (b) Grundl, M. A.; Trauner, D. Org. Lett. 2006, 8, 23.
8. (c) Wipf, P.; Furegati, M. Org. Lett. 2006, 8, 1901.
9. For formal syntheses, see: (a) Jeong, J. H.; Weinreb, S. M. Org. Lett. 2006, 8, 2309.
10. (b) Fürstner, A.; Ackerstaff, J. Chem. Commun. 2008, 2870.
11. (c) Taniguchi, T.; Zaimoku, H.; Ishibashi, H. J. Org. Chem. 2009, 74, 2624.
12. For examples of point-to-planar chirality transfer, see: (a) Evans, D. A.; Dinsmore, C. J.; Watson, P. S.; Wood, M. R.; Richardson, T. I.; Trotter, B. W.; Katz, J. L. Angew. Chem., Int. Ed. 1998, 37, 2704.
13. (b) Layton, M. E.; Morales, C. A.; Shair, M. D. J. Am. Chem. Soc. 2002, 124, 773.
14. (c) Nicolaou, K. C.; Boddy, C. N. C. J. Am. Chem. Soc. 2002, 124, 10451.
15. (d) For examples of planar-to-point chirality transfer, see: Fu, G. C. Acc. Chem. Res. 2006, 39, 853.
16. For an enantioselective route to the starting material for 4, see: Jiricek, J.; Blechert, S. J. Am. Chem. Soc. 2004, 126, 3534.
17. See Supporting Information for details.
18. Bierling, B.; Kirschke, K.; Oberender, H.; Schulz, M. J. Prakt. Chem. 1972, 314, 170.
19. Corey, E. J.; Lazerwith, S. E. J. Am. Chem. Soc. 1998, 120, 12777.
20. Mukaiyama, T.; Matsuo, J.; Kitagawa, H. Chem. Lett. 2000, 29, 1250.