Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 1
1,166
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Highly Efficient and Selective Deprotection Method for Prenyl, Geranyl, and Phytyl Ethers and Esters Using Borontrifluoride–Etherate

, , &
Pages 26-33 | Received 07 Mar 2011, Published online: 05 Sep 2012

REFERENCES

  • (a) Green , T. W. ; Wuts , P. G. M. Protective Groups in Organic Synthesis; 2nd ed. ; John Wiley : New York , 1991 ; (b) Kocieneski , P. J. Protecting Groups ; Thieme : Stuttgart , 1994 .
  • Narender , T. ; Reddy , K. P. A simple and highly efficient method for the synthesis of chalcones by using borontrifluoride–etherate . Tetrahedron Lett. 2007 , 48 , 3177 .
  • Narender , T. ; Reddy , K. P. BF3–Et2O-mediated biogenetic-type synthesis of chromanochalcones from prenylated chalcones via a regioselective cyclization reaction . Tetrahedron Lett. 2007 , 48 , 7628 .
  • Narender , T. ; Reddy , K. P. Shweta BF3-Et2O-mediated one-pot synthesis of acetylchromans from polyhydroxyacetophenones and isoprene/allyl alcohol . Synth. Commun. 2009 , 39 , 384 .
  • Narender , T. ; Reddy , K. P. ; Shweta ; Mishra , D. K. ; Srivastava , K. ; Puri , S. K. Total synthesis of munchiwarin, a triprenylated chalcone from Crotalaria medicagenia . Org. Lett. 2007 , 9 , 5369 .
  • Narender , T. ; Tanvir , K. ; Nishi Goel , N. ; Gupta , S. Synthesis of chromenochalcones and evaluation of their in vitro antileishmanial activity . Biorg. Med. Chem. 2005 , 13 , 6543 .
  • Sinhababu , A. K. ; Kawase , M. ; Borchardt , R. T. t-Butyldimethylsilyl ethers of phenols: Their one-step conversion to benzyl or methyl ethers and utility in regioselective o-lithiation. Tetrahedon Lett. 1987, 28, 4139.
  • Barcelo , G. ; Grenouillat , D. ; Senet , J. P. ; Sennyey , G. Pentaalkylguanidines as etherification and esterification catalysts . Tetrahedron 1990 , 46 , 1839 .
  • Jung , M. E. ; Lyster , M. A. Quantitative dealkylation of alkyl ethers via treatment with trimethylsilyl iodide: A new method for ether hydrolysis . J. Org. Chem. 1977 , 42 , 3761 .
  • Ohsawa , T. ; Hatano , K. ; Kayoh , K. ; Kotabe , J. ; Oishi , T. Quantitative dealkylation of alkyl ethers via treatment with trimethylsilyl iodide: A new method for ether hydrolysis . Tetrahedron Lett. 1992 , 33 , 5555 .
  • Rigby , J. H. ; Mateo , M. E. Total synthesis of (+)-narciclasine . J. Am. Chem. Soc. 1997 , 119 , 12655 .
  • Holcombe , J. L. ; Livinghouse , J. S. A new and specific method for the protection of phenols as the corresponding tert-butyl ethers . J. Org. Chem. 1986 , 51 , 111 .
  • Masada , H. ; Oishi , Y. A new synthesis of aryl t-butyl ethers . Chem. Lett. 1978 , 1 , 57 .
  • Van Heerden , F. R. ; Van Zyl , J. J. ; Rall , G. J. H. ; Brandt , E. V. ; Roux , D. G. Phase-transfer catalysis: A general method of methoxymethylation of the hydroxyl function . Tetrahedron Lett. 1978 , 19 , 661 .
  • Yardley , J. P. ; Fletcher , H. Introduction of the methoxymethyl ether protecting group . Synthesis 1976 , 244 .
  • Rahman , M. A. A. ; Elliott , H. W. ; Binks , R. ; Kung , W. ; Rapoport , H. Synthesis and pharmacology of 6-methylenedihydrodesoxymorphine . J. Med. Chem. 1996 , 9 , 1 .
  • Williams , D. R. ; Barner , B. A. ; Nishitani , K. ; Phillips , J. G. Total synthesis of milbemycin . J. Am. Chem. Soc. 1982 , 104 , 4708 .
  • Falck , J. R. ; Reddy , K. K. ; Chandrasekhar , S. Synthesis and structure revision of the myo-inositol monophosphatase inhibitor L-671,776 . Tetrahedron Lett. 1997 , 38 , 1607 .
  • Corey , E. J. ; Danheiser , R. L. ; Chandrasekaran , S. ; Siret , P. ; Keck , G. E. ; Gras , J. L. Stereospecific total synthesis of gibberellic acid: A key tricyclic intermediate . J. Am. Chem. Soc. 1978 , 100 , 8031 .
  • Leboff , A. ; Carbonnelle , A. C. ; Alazard , J. P. ; Thal , C. ; Kende , A. S. Intramolecular radical coupling of a phenolic enolate: Oxidative fragmentation of the spirodiketone intermediate . Tetrahedron Lett. 1987 , 28 , 4163 .
  • Saimoto , H. ; Kusano , Y. ; Hiyama , T. A mild procedure for hydrolysis of alkoxymethyl aryl ethers to give hydroxyarenes: A rational synthesis of ascofuranone . Tetrahedron Lett. 1986 , 27 , 1607 .
  • Cruz-Almanza , R. ; Perez-Floress , F. J. ; Avila , M. Deprotection of tetrahydropyranyl ethers with a Mexican bentonite: Synthesis of farnesylhydroquinone . Synth. Commun. 1990 , 20 , 1125 .
  • Ballini , R. ; Bigi , F. ; Carloni , S. ; Maggi , R. ; Sartori , G. Solvent-free tetrahydropyranylation of phenols and alcohols over zeolites HSZ as reusable catalysts . Tetrahedron Lett. 1997 , 38 , 4169 .
  • Guibe , F. Allylic protecting groups and their use in a complex environment, part I: Allylic protection of alcohols . Tetrahedron 1997 , 53 , 13509 .
  • Sharma , G. V. M. ; Ilangovan , A. ; Mahalingam , A. K. A mild and highly selective deprotective method of prenyl ethers using ytterbium triflate . J. Org. Chem. 1998 , 63 , 9103 .
  • Babu , K. S. ; Raju , B. C. ; Srinivas , P. V. ; Rao , J. M. Highly efficient and chemoselective cleavage of prenyl ethers using ZrCl4/NaBH4 . Tetrahedron Lett. 2003 , 44 , 2525 .
  • Babu , K. S. ; Raju , B. C. ; Srinivas , P. V. ; Rao , A. S. ; Kumar , S. P. ; Rao , J. M. A simple, effective, and highly selective cleavage of 3-methylbut-2-enyl (prenyl) ethers using p-toluenesulfonic acid . Chem. Lett. 2003 , 32 , 704 – 705 .
  • Sharma , G. V. M. ; Govardhan Reddy , C. ; Radhakrishna , P. A simple and efficient protocol for the deprenylation of ethers and esters catalysed by zirconium(IV) chloride–sodium iodide. Synlett 2003, 1728.
  • Tsuritani , T. ; Shinokubo , H. ; Oshima , K. Highly selective cleavage of prenyl ethers by means of a TiCl4-n-Bu4NI mixed reagent . Tetrahedron Lett. 1999 , 40 , 8121 .
  • Vatele , J. M. Iodine in dichloromethane—A simple method for selective cleavage of prenyl ethers . Synlett 2001 , 1989 .
  • Vatele , J. M. An efficient and chemoselective cleavage of prenyl ethers with DDQ . Synlett 2002 , 507 .
  • Cossy , J. ; Albouy , A. ; Scheloske , M. ; Pardo , G. A very useful and mild method for the protection and deprotection of carboxylic acids . Tetrahedron Lett. 1994 , 35 , 1539 .
  • Yadav , J. S. ; Subba Reddy , B. V. ; Rao , C. V. ; Chand , P. K. ; Prasad , A. R. A facile and selective cleavage of prenyl esters catalyzed by CeCl3 · 7H2O-NaI . Synlett 2002 , 137 .
  • Ramesh , C. ; Mahender , G. ; Ravindranath , N. ; Das , B. A simple, mild and efficient procedure for selective cleavage of prenyl esters using silica-supported sodium hydrogen sulphate as a heterogenous catalyst . Tetrahedron Lett. 2003 , 44 , 1465 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.