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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 21
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Original Articles

(±)-3,4,4a,5,6,7-Hexahydro-4a-Methyl-7,7-Diphenyl-1(2H)-Naphthtlenone

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Pages 4081-4089 | Published online: 23 Aug 2006

References

  • Apsimon , J. W. , Fyfe , K. E. and Greaves , A. M. 1984 . The Total Synthesis of Natural Products , Vol. 6 , 85 – 139 . NY : Wiley-Interscience . The DE rings of several triterpenes incorporate the 3,4,4a,5,6,7-hexahydro-4a,7,7-trimethyl-1(2H)-naphthalenone ring skeleton, see
  • Meyer , W. L. , Brannon , M. J. , Burgos , C. G. , Goodwin , T. E. and Howard , R. W. 1985 . J. Org. Chem. , 50 : 438 – 447 . One other potential approach to the synthesis of fused rings bearing 7,7-disubstitution was deemed unsuitable because of steric hindrance to the initial Michael addition, see
  • Bunce , R. A. and Childress , R. S. 1995 . Org. Prep. Proc. Int. , 26 : 709 – 713 .
  • Bunce , R. A. and Childress , R. S. 1995 . Org. Prep. Proc. Int. , 26 : 122 – 125 .
  • The Grignard reagent of 1-bromo-3,3-diphenyl-4-pentene could not be produced under standard conditions (Mg, THF, reflux). Exposure of the bromide to Rieke magnesium at 0°C for 30 min followed by quenching with aq. NH4Cl resulted in recovery of 22% of the unreacted bromide, 37% of 3,3-diphenyl-1-pentene (quenched Grignard), 6% of 1,1-diphenylpropene (fragmented Grignard), and 20% of a mixture of dimers along with several unidentified minor compounds which could not be isolated in pure form
  • Paquette , L. A. and Poupart , M.-A. 1993 . J. Org. Chem. , 58 : 4245 – 4253 .
  • Molander , G. A. and McKie , J. A. 1991 . J. Org. Chem. , 56 : 4112 – 4120 .
  • Duncan , D. R. 1939 . Inorganic Syntheses , Edited by: Booth , H. S. Vol. 1 , 151 – 152 . New York : McGraw-Hill . gave yields in the 25–40% range. The results for this reaction were best when commercial anhydrous HBr (Matheson) was used. The use of HBr generated by addition of Br2 to tetralin
  • Adelstein , G. W. , Yen , C. H. , Dajani , E. Z. and Bianchi , R. G. 1976 . J. Med. Chem. , 19 : 1221 – 1225 .
  • Buschmann , E. and Zeeh , B. 1979 . Liebig's Ann. Chem. , : 1585 – 1590 .

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