NaOAc-mediated selective deprotection of aromatic acetates and Its application in the synthesis of natural products

Synthetic Communications

Volumn 39, Issue 11, 2009, Pages 1949-1956

  Narender, T ^a   Reddy, K Papi ^a   Madhur, G ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Aromatic acetates; Deacetylation reaction; Flavanone; NaOAc; Prenylatedchalcones; Selective deprotection

Indexed keywords

ACETIC ACID DERIVATIVE; ANTIPARASITIC AGENT; CHALCONE DERIVATIVE; FLAVANONE DERIVATIVE; NATURAL PRODUCT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DEACYLATION; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 67650078987     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802621731     Document Type: Article

References (13)

1. (a) Narender, T.; Shweta; Tanvir, K.; Rao, M. S.; Srivastava, K.; Puri, S. K. Prenylated chalcones isolated from Crotalaria genus inhibits in vitro growth of the human malaria parasite Plasmodium falciparum. Bioorg. Med. Chem. Lett. 2005,15,2453-2455;
2. (b) Kumar, J. K.; Narender, T.; Rao, M. S.; Rao, P. S.; Toth, G.; Balazs, B.; Duddeck, H. Further dihydrochalcones from the Crotalaria ramo- sissima. J. Braz. Chem. Soc. 1999,10, 278-280;
3. (c) Narender, T.; Shweta; Gupta, S. A convenient and biogenetic type synthesis of few naturally occurring chro- meno dihydrochalcones and their in vitro antileishmanial activity. Bioorg. Med. Chem. Lett. 2004, 14, 3913-3916;
4. (d) Narender, T.; Tanvir, K.; Shweta; Nishi; Goyal, N.; Gupta, S. Synthesis of chromenochalcones and evaluation of their in vitro antileishmanial activity. Bioorg. Med. Chem. 2005,13, 6543-6550.
5. (a) Kunitake, T.; Okahata, Y.; Sakamoto, T. Multifunctional hydrolytic catalyses, 8: Remarkable acceleration of the hydrolysis of p-nitrophenyl acetate by micellar bifunctional catalysts. J. Am. Chem. Soc. 1976, 98, 7799-7806;
6. (b) Gonzalez, A. G.; Jorge, Z. D.; Dorta, H. L.; Rodriguez, F. L. Deacylation of aromatic acetates: A new method of selective protection of the hydroxyl function. Tetrahedron Lett. 1981, 22, 335-336;
7. (c)Tee, O. S.; Mazza, C.; LeZano-Hemmer, R.; Giorgi, I. B. Ester cleavage by cyclodextrins in aqueous dimethyl sulfoxide mixtures: Substrate binding versus transition state binding.J. Org. Chem. 1994, 59,7602-7608;
8. (d) Crampton, M. R.; Holt, K. E.; Perey, J.M. 1-(2-Acetoxyethoxy)-2,4,6- trinitrobenzene: A new substrate for enzyme catalysed hydrolysis. J. Chem. Soc., Perkin Trans. 2 1990, 1701;
9. (e) Beisselier, V. L.; Postal, M.; Dunach, E. Bi(III) as new catalyst for the selective hydrolysis of esters. Tetrahedron Lett. 1997, 38, 2981-2984;
10. (f) Guo, J.; Huang, W.; Scanlan, T. S. Kinetic and mechanistic characterization of an efficient hydro- lytic antibody: Evidence for the formation of an acyl intermediate. J. Am. Chem. Soc. 1994, 116, 6062-6069;
11. (g) Ramesh, C.; Mahender, G.; Ravindra- nath, N.; Das, B. A mild, highly selective and remarkably easy procedure for deprotection of aromatic acetates using ammonium acetate as a neutral catalyst in aqueous medium. Tetrahedron 2003, 59, 1049-1054;
12. (h)Das, B.; Joydeep, J.; Ramu, R.; Pal, R.; Ravindranath, N.; Ramesh, C. Efficient, selective deprotection of aromatic acetates catalyzed by amberlyst-15 or iodine. Tetrahedron Lett. 2003, 44, 5465-5468;
13. (i) Bandgar, B. P.; Uppalla, L. S.; Sagar, A. D.; Sadavarte, V. S. A mild procedure for rapid and selective deprotection of aryl acetates using natural kaolinitic clay as a reusable catalyst. Tetrahedron Lett. 2001, 42, 1163-1165.