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Original Articles

SYNTHESIS OF THE HAMIGERANS. A REVIEW

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Pages 1-35 | Received 26 Oct 2004, Accepted 05 Jan 2005, Published online: 09 Feb 2009

References

  • Wellington , K. D. , Cambie , R. C. , Rutledge , P. S. and Bergquist , P. R. 2000 . J. Nat. Prod. , 63 : 79
  • Searle , P. A. and Molinski , T. F. 1995 . J. Am. Chem. Soc. , 117 : 8126
  • Molinski , T. F. 1996 . Tetrahedron Lett. , 37 : 7879
  • Casapullo , A. , Minale , L. , Zollo , F. and Lavayre , J. 1994 . J. Nat. Prod. , 57 : 1227
  • Cambie , R. C. , Rickard , C. E. F. , Rutledge , P. S. and Wellington , K. D. 2001 . Acta Cryst. , C57 : 958
  • Nicolaou , K. C. , Gray , D. and Tae , J. 2001 . Angew. Chem. Int. Ed. , 40 : 3675
  • Nicolaou , K. C. , Gray , D. and Tae , J. 2001 . Angew. Chem. Int. Ed. , 40 : 3679
  • Nicolaou , K. C. , Gray , D. L. F. and Tae , J. 2004 . J. Am. Chem. Soc. , 126 : 613
  • Fujisaki , S. , Eguchi , H. , Omura , A. , Okamoto , A. and Nishida , A. 1993 . Bull. Chem. Soc. Jpn. , 66 : 1576
  • Krohn , K. , Bernard , S. , Flörke , U. and Hayat , N. 2000 . J. Org. Chem. , 65 : 3218
  • Clive , D. L. J. and Wang , J. 2003 . Angew. Chem. Int. Ed. , 42 : 3406
  • Clive , D. L. J. and Wang , J. 2003 . Tetrahedron Lett. , 44 : 7731
  • Clive , D. L. J. and Wang , J. 2004 . J. Org. Chem. , 69 : 2773
  • Beckwith , A. L. J. , Phillipou , G. and Serelis , A. K. 1981 . Tetrahedron Lett. , 22 : 2811
  • RajanBabu , T. V. and Fukunaga , T. 1989 . J. Am. Chem. Soc. , 111 : 296
  • Gansäuer , A. and Pierobon , M. 2000 . Synlett , : 1357
  • Cooke , R. G. and Dowd , H. 1953 . Aust. J. Chem. , 6 : 53
  • Ruzicka , L. , Hösli , H. and Hofmann , K. 1936 . Helv. Chim. Acta , 19 : 370 Cf.
  • Yatabe , T. , Kayakiri , H. , Kawai , Y. , Oku , T. and Tanaka , H. 1998 . Chem. Pharm. Bull. , 46 : 1556 Cf.
  • Freifelder , M. 1978 . Catalytic Hydrogenation in Organic Synthesis. Procedures and Commentary , 15 New York : Wiley .
  • Rylander , P. N. 1967 . Catalytic Hydrogenation over Platinum Metals , 91 New York : Academic Press .
  • Gray , A. C. G. and Hart , H. 1968 . J. Am. Chem. Soc. , 90 : 2569 Examples of hydrogenation of tetrasubstituted double bonds conjugated with benzene rings are known (Beilstein database); see, especially
  • Martin , S. F. 1980 . Tetrahedron , 36 : 419 Reviews on construction of quaternary centers
  • Fuji , K. 1993 . Chem. Rev. , 93 : 2037
  • Corey , E. J. and Guzman-Perez , A. 1998 . Angew. Chem., Int. Edn. , 37 : 388
  • Christoffers , J. and Mann , A. 2001 . Angew. Chem., Int. Edn. , 40 : 4591
  • Sannigrahi , M. 1999 . Tetrahedron , 55 : 9007
  • Snyder , L. and Meyers , A. I. 1993 . J. Org. Chem. , 58 : 7507
  • Sandham , D. A. and Meyers , A. I. 1995 . J. Chem. Soc., Chem. Commun. , : 2511
  • Burgess , L. E. and Meyers , A. I. 1992 . J. Org. Chem. , 57 : 1656 Cf.
  • Clive , D. L. J. , Yu , M. and Sannigrahi , M. 2004 . J. Org. Chem. , 69 : 4116
  • Gaunt , M. J. , Yu , J. and Spencer , J. B. 1998 . J. Org. Chem. , 63 : 4172 For studies on the mechanism of hydrogenolysis, see
  • Colvin , E. 1981 . Silicon in Organic Synthesis , 12 London : Butterworth's .
  • Connoly , T. J. and Durst , T. 1997 . Tetrahedron , 53 : 15969
  • Mateus , C. R. , Almeida , W. P. and Coelho , F. 2000 . Tetrahedron Lett. , 41 : 2533
  • Trost , B. M. , Greenspan , P. D. , Yang , B. V. and Saulnier , M. G. 1990 . J. Am. Chem. Soc. , 112 : 9022
  • Mehta , G. and Shinde , H. M. 2003 . Tetrahedron Lett. , 44 : 7049
  • Mehta , G. , Krishnamurthy , N. and Karra , S. R. 1991 . J. Am. Chem. Soc. , 113 : 5765
  • It is not clear if only one alcohol is formed.
  • Details indicating whether in each case a single alcohol or (more likely) a mixture of alcohols was formed have not yet been published.
  • It is not clear from our reading of the text if the yield (55-60%) refers exclusively to ring-closed products or includes also the reduction products.
  • Trost , B. M. , Pissot-Soldermann , C. , Chen , I. and Schroeder , G. M. 2004 . J. Am. Chem. Soc. , 126 : 4480
  • Nishimura , S. , Sakamoto , H. and Ozawa , T. 1973 . Chem. Lett. , 855
  • Piers , E. and Lau , S. Y. W. Abstracts of Papers, 227th ACS National Meeting . March 28-April 1 , Anaheim, CA, , United States (ORGN-427)

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