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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 1, 1971 - Issue 4
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Original Articles

Lead Tetraacetate Fragmentation of Loganin Aglucone O-Metheyl Ether and its Stereoisomers

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Pages 233-240 | Received 30 Sep 1971, Published online: 06 Feb 2007

References

  • Lj Mihailović , M. and Caković , Z. 1970 . Synthesis , : 209 For a recant review sea
  • Büchi , G. , Carlson , J. A. , Powell , J. S. Jr. and Tietze , L.-F. 1970 . J. Amer. Chem. Soc. , 92 : 2165 A.R. Battersby, E.S. Hall and R. Southgate, J. Chem. Soc. (C), 721 (1969)
  • Acetate 5 was converted by Büchi and co-workers2 into loganin, a natural product of known absolute stereochemistry.
  • Housler , K. and Kalvoda , J. 1964 . Angew. Chem. Int. Ed. , 3 : 525 For similar cases of radical induced epimerization of alcohols see and A. Nickon, F.J. McGuire, J.R. Mahajan, B. Umezawa, and S.A. Narang, J. Amer. Chem. Soc., 86, 1437 (1964)
  • Other isolated products included ketone 17, starting material, and the corresponding acetate derivative
  • All new compounds reported in this paper have been fully characterized by ir, uv, nmr, and mass spectrometry as well as combustion analysis. The structural formulas depict one diastereoisomer, but refer to racamic compounds throughout.

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