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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 15
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Original Articles

Novel Domino Reactions of (Z,Z)-2,2′-Thiobis(1,3-diarylprop-2-en-1-ones) with Acetylacetone and Ethyl Acetoacetate: Stereoselective Synthesis of Highly Functionalized Dihydrofurans

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Pages 2776-2788 | Received 17 Sep 2008, Published online: 26 Jun 2009

REFERENCES

  • (a) Gnanadeepam , M. ; Selvaraj , S. ; Perumal , S. ; Hewlins , M. J. E. ; Lycka , A. 2,6-Diaroyl-3,5-diaryl-4-methyltetrahydro-1,4-thiazine-1,1-dioxides–A synthetic and stereochemical study . Phosphorus, Sulfur Silicon Relat. Elem. 1999 , 155 , 167 – 173 ; (b) Selvaraj , S. ; Renuga , S. ; Gnanadeepam , M. ; Perumal , S. ; Sivakolunthu , S. Synthesis and stereochemical studies of some 4,4-diethoxycarbonyl-2,6-diaroyl-3,5-diarylthiane-1,1-dioxides . Indian J. Chem. 1999 , 38B , 376 – 377 ; (c) Gnanadeepam , M. ; Renuga , S. ; Selvaraj , S. ; Perumal , S. ; Hewlins , M. J. E. Synthesis and NMR spectral studies of 2e,6e-diaroyl-3e,5e-diaryl-1,4-dithiane-1,1-dioxides . Phosphorus, Sulfur Silicon Relat. Elem. 1998 , 134/135 , 171 – 176 .
  • Renuga , S. ; Selvaraj , S. ; Perumal , S. ; Hewlins , M. J. E. Diastereoselective synthesis of 2,2′-thiobis- and 2,2′-sulfonylbis-(2-aroyl-3-aryloxiranes) . Tetrahedron 1999 , 55 , 9309 – 9316 .
  • (a) Renuga , S. ; Selvaraj , S. ; Perumal , S. ; Lycka , A. ; Gnanadeebam , M. Diastereoselective synthesis and 1H and 13C NMR study of 4-acetyl-2,6-diaroyl-3,5-diaryl-4-ethoxycarbonylthiane-1,1-dioxides . Magn. Reson. Chem. 2001 , 39 , 651 – 653 ; (b) Renuga , S. ; Perumal , S. ; Gnanadeepam , M. Department of Chemistry, Fatima College, Madurai. Unpublished results .
  • (a) Matsuda , H. ; Ohara , K. ; Morii , Y. ; Hashimoto , M. ; Miyairi , K. ; Okuno , T. α-Selective glycosylation with 5-thioglucopyranosyl donors: Synthesis of an isomaltotetraoside mimic composed of 5-thioglucopyranose units. Bioorg. Med. Chem. Lett. 2003, 1063; (b) Bozo , E. ; Boros , S. ; Kuszmann , J. Conversion of 2,6-anhydro-D-altrose and -mannose derivatives with 4-substituted phenyl thiols to prepare compounds with potential antithrombotic activity. Carbohydr. Res. 2001, 332, 325–333; (c) Bozo , E. ; Boros , S. ; Kuszmann , J. Synthesis of 4-substituted phenyl 3,6-anhydro-1,3-dithio-D-glucofuranosides and -pyranosides as well as 2,6-anhydro-1,2-dithio-α-D-altrofuranosides possessing antithrombotic activity. Carbohydr. Res. 2000, 329, 525–538.
  • (a) Tietze , L. F. ; Brasche , G. ; Gericke , K. Domino Reactions in Organic Synthesis ; Wiley-VCH : Weinheim , Berlin , 2006 ; (b) Mondal, S.; Malik, C. K.; Ghosh, S. A novel asymmetric approach to a densely functionalized lactarane ring system through a domino ring opening–ring closing metathesis of a norbornene derivative. Tetrahedron Lett. 2008, 49, 5649–5651 .
  • (a) Takadoi , M. ; Katoh , T. ; Ishiwata , A. ; Terashima , S. A novel total synthesis of (+)-himbacine, a potent antagonist of the muscarinic receptor of M2 subtype . Tetrahedron Lett. 1999 , 40 , 3399 – 3402 ; (b) Bruggemann , M. ; McDonald , A. I. ; Overman , L. E. ; Rosen , M. D. ; Schwink , L. ; Scott , J. P. Total synthesis of (±)-didehydrostemofoline (asparagamine A) and (±)-isodidehydrostemofoline . J. Am. Chem. Soc. 2003 , 125 , 15284 – 15285 .
  • Rao , C. B. S. Chemistry of Lignans ; Andhra University Press : Waltair , 1978 .
  • (a) de March , P. ; Figueredo , M. ; Font , J. ; Raya , J. Highly efficient, enantioselective synthesis of (+)-grandisol from a C 2-symmetric bis(α,β-butenolide) . Org. Lett. 2000 , 2 , 163 – 165 ; (b) Harcken , C. ; Bruckner , R. Synthesis of optically active butenolides and γ-lactones by the Sharpless asymmetric dihydroxylation of β,γ-unsaturated carboxylic esters . Angew. Chem., Int. Ed. 1997 , 36 , 2750 – 2752 .
  • (a) Fraga , B. M. Natural sesquiterpenoids . Nat. Prod. Rep. 1992 , 9 , 217 – 241 ; (b) Merritt , A. T. ; Ley , S. V. Clerodane diterpenoids . Nat. Prod. Rep. 1992 , 9 , 243 – 287 ; (c) Mortensen , D. S. ; Rodriguez , A. L. ; Carlson , K. E. ; Sun , J. ; Katzenellenbogen , B. S. ; Katzenellenbogen , J. A. Synthesis and biological evaluation of a novel series of furans: Ligands selective for estrogen receptor α . J. Med. Chem. 2001 , 44 , 3838 – 3848 .
  • (a) Navarro , E. ; Alonso , S. J. ; Trujillo , J. ; Jorge , E. ; Perez , C. General behavior, toxicity, and cytotoxic activity of elenoside, a lignan from Justicia hyssopifolia. J. Nat. Prod. 2001 , 64 , 134 – 135 ; (b) Joseph , H. ; Gleye , J. ; Moulis , C. ; Mensah , L. J. ; Roussakis , C. ; Gratas , C. Justicidin B, a cytotoxic principle from Justicia pectoralis. J. Nat. Prod. 1988 , 51 , 599 – 600 .
  • Cho , J. Y. ; Baik , K. U. ; Yoo , E. S. ; Yoshikawa , K. ; Park , M. H. In vitro antiinflammatory effects of neolignan woorenosides from the rhizomes of Coptis japonica. J. Nat. Prod. 2000 , 63 , 1205 – 1209 .
  • Borsato , M. L. C. ; Grael , C. F. F. ; Souza , G. E. P. ; Lopes , N. P. Analgesic activity of the lignans from Lychnophora ericoides. Phytochemistry 2000 , 55 , 809 – 813 .
  • Kemp , M. S. ; Burden , R. S. Phytoalexins and stress metabolites in the sapwood of trees. Phytochemistry 1986, 25, 1261–1269.
  • da Silva Filho , A. A. ; Albuquerque , S. ; Silva , M. L. A. ; Eberlin , M. N. ; Tomazela , D. M. ; Bastos , J. K. Tetrahydrofuran lignans from Nectandra megapotamica with trypanocidal activity . J. Nat. Prod. 2004 , 67 , 42 – 45 .
  • Hislop , J.-A. ; Hunt , M. B. ; Fielder , S. ; Rowan , D. D. Synthesis of deuterated γ-lactones for use in stable isotope dilution assays . J. Agric. Food Chem. 2004 , 52 , 7075 – 7083 .
  • (a) Garzino , F. ; Méou , A. ; Brun , P. Asymmetric radical synthesis of 2,5-diaryl-2,3-dihydrofurans—Application to the preparation of (+)-phyltetralin . Eur. J. Org. Chem. 2003 , 1410 – 1414 ; (b) Lipshutz , B. H. Five-membered heteroaromatic rings as intermediates in organic synthesis . Chem. Rev. 1986 , 86 , 795 – 819 .
  • (a) Chuang , C.-P. ; Tsai , A.-I. Pyridinium ylides in the synthesis of 2,3-dihydrofurans . Synthesis 2006 , 675 – 679 ; (b) Cao , W. ; Chen , G. ; Chen , J. ; Chen , R. Simple approach to the high stereoselective synthesis of trans-2,3-dihydrofuran derivatives . Synth. Commun. 2005 , 35 , 527 – 533 ; (c) Yang , Z. ; Fan , M. ; Mu , R. ; Liu , W. ; Liang , Y. A facile synthesis of highly functionalized dihydrofurans based on 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed reaction of halides with enones . Tetrahedron 2005 , 61 , 9140 – 9146 ; (d) Yang , Z. ; Fan , M. ; Liu , W. ; Liang , Y. A novel facile synthetic route to highly substituted 2,3-dihydrofurans via ammonium ylides . Synthesis 2005 , 2188 – 2192 .
  • Nandhini , M. S. ; Krishnakumar , R. V. ; Mostad , A. ; Renuga , S. ; Selvaraj , S. ; Perumal , S. Natarajan , S. trans-3-Acetyl-5-benzoyl-2-methyl-4-phenyl-4,5-dihydrofuran at 150 K . Acta Cryst. 2003 , E59 , o1321 – o1323 .
  • Gnanadeebam , M. ; Renuga , S. ; Selvaraj , S. ; Perumal , S. ; Dhanabalan , A. ; Hewlins , M. J. E. Diastereoselective synthesis of 2,2′-thiobis- and 2,2′-sulfonylbis-(1,3-diarylprop-2-en-1-ones)-an oxidative configurational switch . Phosphorus, Sulfur Silicon Relat. Elem. 2004 , 179 , 203 – 214 .

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