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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 6, 1976 - Issue 3
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Original Articles

Total Synthesis of (+)-CIS- and (+)-Trans-Sativenediol

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Pages 221-226 | Received 19 Dec 1975, Published online: 13 Dec 2006

References

  • Dorn , F. , Bernasconi , P. and Arigoni , D. 1975 . Chimia , 29 : 24
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  • Dorn , F. and Arigoni , D. 1975 . Experientia , 31 : 753
  • We are very grateful to Professors Marumo and Arigoni for personal communications regarding this point. We also wish to thank Professor Arigoni for full experimental details regarding the work which he and his coworkers have done in this area.
  • Piers , E. , Geraghty , M. B. and Soucy , M. 1973 . Syn. Commun. , 3 : 401
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  • All new compounds exhibited spectral data in full accord with the assigned structures and gave satisfactory elemental analysis.
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  • In addition, there was obtained some of the carboxylic acid 10 which could also be converted, by treatment with oxalyl chloride in benzene, into the ketone 8. The combined overall yield of the latter compound was about 55%.
  • Alternative oxidation procedures for the direct conversion of 6 into 8 proved less satisfactory. For example, pyridinium chlorochromate, a reagent very recently employed to oxidatively cyclize citronellol to pulegone18 produced in our case only a good yield of the aldehyde 7, even in the presence of excess reagent.
  • Corey , E. J. and Suggs , J. W. 1975 . Tetrahedron Lett. , : 2647
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  • We are very grateful to Professor Marumo for copies of the i.r. and p.m.r. spectra of (-)-cis-sativenediol (1) and of (-)-isosativenediol (3).

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