Syntheses and biological evaluation of b-ring-modified analogues of dafachronic acid A

Organic Letters

Volumn 10, Issue 16, 2008, Pages 3643-3645

  Giroux, Simon ^a   Bethke, Axel ^b   Fielenbach, Nicole ^b   Antebi, Adam ^b   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

^b BAYLOR COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAENORHABDITIS ELEGANS PROTEIN; CELL RECEPTOR; DAF 12 PROTEIN, C ELEGANS; DAF-12 PROTEIN, C ELEGANS; DAFACHRONIC ACID A; DRUG DERIVATIVE; ERGOSTEROL; LIGAND;

ANIMAL; ARTICLE; CAENORHABDITIS ELEGANS; CHEMISTRY; CONFORMATION; DRUG EFFECT; GENETIC TRANSCRIPTION; GENETICS; STEREOISOMERISM; SYNTHESIS;

ANIMALS; CAENORHABDITIS ELEGANS; CAENORHABDITIS ELEGANS PROTEINS; ERGOSTEROL; LIGANDS; MOLECULAR CONFORMATION; RECEPTORS, CYTOPLASMIC AND NUCLEAR; STEREOISOMERISM; TRANSCRIPTION, GENETIC;

EID: 54049097181     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801425v     Document Type: Article

References (12)

1. (a) Motola, D. L.; Cummins, C. L.; Rottiers, V.; Sharma, K. K.; Li, T.; Li, Y.; Suino-Powell, K.; Xu, H. E.; Auchus, R. J.; Antebi, A.; Mangelsdorf, D. J. Cell 2006, 124, 1209-1223.
2. (b) Gerisch, B.; Rottiers, V.; Li, D.; Motola, D. L.; Cummins, C. L.; Lehrach, H.; Mangelsdorf, D. J.; Antebi, A. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 5014-5019.
3. (c) Rottiers, V.; Motola, D. L.; Gerisch, B.; Cummins, C. L.; Nishiwaki, K.; Mangelsdorf, D. J.; Antebi, A. Developmental Cell 2006, 10, 473-482.
4. (d)(c) For an online resource on C. elegans, see: http://www.wormbook.org.
5. Giroux, S.; Corey, E. J. J. Am. Chem. Soc. 2007, 129, 9866-9867.
6. Giroux, S.; Corey, E. J. Org. Lett. 2008, 10, 801-802.
7. -12 g/mL as a hatching factor for H. glycines; see: (a) Fukuzawa, A.; Furusaki, A.; Ikura, M.; Masamune, T. J. Chem. Soc. Chem. Commun. 1985, 221-222, 748.
8. (b) Masamune, T.; Anetai, M.; Takasugi, M.; Katsui, N. Nature 1982, 297, 495-496.
9. For the syntheses of glycinoeclepin A, see: (a) Murai, A; Tanimoto, N.; Sakamoto, N.; Masamune, T. J. Am. Chem. Soc. 1988, 110, 1985-1986.
10. 7 double bonds has been reported in the literature.
11. (b) Mori, K.; Watanabe, H. Pure Appl. Chem. 1989, 61, 543-546.
12. (c) Corey, E. J.; Houpis, I. N. J. Am. Chem. Soc. 1990, 112, 8997-8998.