Selective 3- and 6-OH modification of (-)-clausenamide

Chinese Chemical Letters

Volumn 22, Issue 7, 2011, Pages 761-764

  Xue, Jian Jun ^a   Yu, Xiao Ming ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

( ) Clausenamide; Alzheimer's disease; Derivatives; Synthesis

Indexed keywords

EID: 79957473376     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2011.01.026     Document Type: Article

References (10)

1. M.H. Yang, Y.H. Cao, and W.X. Li Acta Pharmacol. Sin. 22 1 1987 33
2. W. Hartwig, and L. Born J. Org. Chem. 52 1987 4352
3. J.T. Zhang, and X.Y. Jiang Collection of the Academic Papers of Scientific Annual Meeting of Peking Union Medical College 1994 Beijing Medical University & Peking Union Medical College Publishing House Beijing 356
4. Z. Feng, X. Li, and G. Zheng Bioorg. Med. Chem. Lett. 19 8 2009 2112
5. E.J. Corey, and A. Venkateswarlu J. Am. Chem. Soc. 94 17 1972 6190
6. W.G. Dauben, and G.A. Boswell J. Am. Chem. Soc. 83 24 1961 5003
7. The trans geometry between 3-OH and 4-Ph was validated by 1H NMR of 12; (S)-(-)-O-actylmandelation of compound 4 was carried out later and only one product was detected by 1H NMR of the reaction mixture, therefore the possible C-3 epimerization could be precluded.
8. H.S. Park, H.Y. Lee, and Y.H. Kim Org. Lett. 7 15 2005 3187
9. The proportions of the two compounds were determined by 1H NMR of the mixture.
10. 2 282.1494, found 282.1501.