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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 11
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Original Articles

NaOAc-Mediated Selective Deprotection of Aromatic Acetates and Its Application in the Synthesis of Natural Products

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Pages 1949-1956 | Received 24 Sep 2008, Published online: 27 Apr 2009

REFERENCES

  • (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 ; (b) Kumar , J. K. ; Narender , T. ; Rao , M. S. ; Rao , P. S. ; Toth , G. ; Balazs , B. ; Duddeck , H. Further dihydrochalcones from the Crotalaria ramosissima . J. Braz. Chem. Soc. 1999 , 10 , 278 – 280 ; (c) Narender , T. ; Shweta ; Gupta , S. A convenient and biogenetic type synthesis of few naturally occurring chromeno dihydrochalcones and their in vitro antileishmanial activity . Bioorg. Med. Chem. Lett. 2004 , 14 , 3913 – 3916 ; (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 .
  • (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 ; (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 ; (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 ; (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 ; (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 ; (f) Guo , J. ; Huang , W. ; Scanlan , T. S. Kinetic and mechanistic characterization of an efficient hydrolytic antibody: Evidence for the formation of an acyl intermediate . J. Am. Chem. Soc. 1994 , 116 , 6062 – 6069 ; (g) Ramesh , C. ; Mahender , G. ; Ravindranath , 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 ; (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 ; (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 .
  • CDRI Communication No. 7574.

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