A simplified synthesis of the diastereomers of Levuglandin E2

Synthetic Communications

Volumn 35, Issue 3, 2005, Pages 397-408

  Amarnath, Venkataraman ^a   Amarnath, Kalyani ^a   Masterson, Tina ^a   Davies, Sean ^a   Roberts II, Jackson ^a  

^a VANDERBILT UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

Dimethyl acetal of reactive aldehyde; Levuglandin E2; Montmorillonite deprotection

Indexed keywords

2,2 DIMETHOXYETHANAL; ACETAL; ACETALDEHYDE; DIMETHYLACETAL; FREE RADICAL; LEVUGLANDIN E2; MONTMORILLONITE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHEMICAL ANALYSIS; DRUG ISOLATION; HYDROLYSIS; ISOTOPE LABELING; PHASE SEPARATION; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 14644399882     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200048945     Document Type: Article

References (18)

1. Salomon, R. G.; Miller, D. B.; Zagorski, M. G.; Coughlin, D. J. Solvent-induced fragmentation of prostaglandin endoperoxides. J. Am. Chem. Soc. 1984, 106, 6049-6060.
2. Brame, C. J.; Salomon, R. G.; Marrow, J. D.; Roberts, L. J., II. Identification of extremely reactive γ-ketoaldehydes (isolevuglandins) as products of the isoprostane pathway and characterization of their lysyl protein adducts. J. Biol. Chem. 1999, 274, 13139-13146.
3. 2-isoprostane pathway. Chem. Phys. Lipids 2004, 128, 85-99.
4. 2 with proteins. Prostaglandins 1987, 34, 643-656.
5. Davies, S. S.; Amarnath, V.; Montine, K. S.; Bernoud-Hubac, N.; Boutaud, O.; Montine, T. J.; Roberts, L. J., II. Effects of reactive γ- ketoaldehydes formed by the isoprostane pathway (isoketals) and cyclooxygenase pathway (levuglandins) on proteasome function. FASEB J. 2002, 16, 715-717.
6. 2. J. Org. Chem. 1990, 55, 3164-3175.
7. Haberli, A.; Pfander, H. Synthesis of bixin and three minor carotenoids from Annatto. Helv. Chem. Acta 1999, 82, 696-706.
8. Hubschwerlen, C.; Specklin, J.; Higelin, J. L-(S)-Glyceraldehyde acetonide. Org. Synth. 1995, 72, 1-5.
9. 2α ethyl ester. J. Org. Chem. 1997, 62, 194-198.
10. Corbe, B.; L'Hostis-Kervella, I.; Haelter, J. On a safe and practical method for the preparation of β-ketophosphonates. Synth. Commun. 1996, 26, 2561-2568.
11. Batten, R. J.; Dixon, A. J.; Taylor, R. J.K. A new method for removing the t-butyl-dimethylsilyl protecting group. Synthesis 1980, 234-236.
12. 2t-isoprostane. J. Org. Chem. 2001, 66, 1876-1884.
13. Greene, T. W.; Wuts, P. G.M. Protective Groups in Organic Chemistry; Wiley: New York, 1999, pp. 299-310.
14. Gautier, E. C. L.; Graham, A. E.; McKillop, A.; Standen, S. P.; Taylor, R. J. K. Acetal and ketal deprotection using Montmorillonite K-10. Tetrahedron Lett. 1997, 38, 1881-1884.
15. 2 methyl ester. J. Am. Chem. Soc. 1988, 110, 4726-4735.
16. Behling, J. R.; Babiak, K. A.; Ng, J. S.; Campbell, A. L.; Moretti, R.; Koerner, M.; Lipshutz, B. H. In situ cuprate formation via transmetalation between vinylstannanes and higher order cyanocuprates. J. Am. Chem. Soc. 1988, 110, 2641-2643.
17. 2. J. Org. Chem. 1997, 62, 7658-7666.
18. West, J. D.; Ji, C.; Duncan, S.; Amarnath, V.; Schneider, C.; Rizzo, C.; Brash, A. R.; Marnett, L. J. Induction of apoptosis in colorectal carcinoma cells treated with 4-hydroxy-2-nonenal and structurally related aldehyde products of lipid peroxidation. Chem. Res. Toxicol. 2004, 17, 453-462.