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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 9
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Original Articles

An Efficient and Stereoselective Total Synthesis of (+/-)-Serricornine

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Pages 981-993 | Published online: 05 Dec 2006

References

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  • Mori , M. , Chuman , T. , Kohno , M. , Kato , K. , Noguchi , M. , Nomi , H. and Mori , K. 1982 . Tetrahedron Lett. , : 667
  • Chuman , T. , Kato , K. and Noguchi , M. 1979 . Agric. Biol. Chem. , 43 : 2005
  • Ono , M. , Onishi , I. , Chuman , T. , Kohno , M. and Kato , K. 1980 . Agric. Biol. Chem. , 44 : 2259
  • Chuman , T. , Mochizuki , K. , Mori , M. , Kohno , M. , Kato , K. and Noguchi , M. 1985 . J. Chem. Ecol. , 11 : 417 and references therein
  • Bartlett , P. A. , Richardson , D. P. and Myerson , J. 1984 . Tetrahedron , 40 : 2317 For stereoselective total synthesis of racemic serricornine, see:
  • For stereoselective total synthesis of optically pure serricornine, see: ref. 2a;
  • Mori , M. , Chuman , T. , Kato , K. and Mori , K. 1982 . Tetrahedron Lett. , : 4593
  • Mori , K. and Watanabe , H. 1985 . Tetrahedron , 41 : 3423
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  • Recently the optically pure lactone (-)-10 has been employed in the total synthesis of natural serricornine. See ref. 4e and 4f.
  • Heathcock , C. H. , Buse , C. T. , Kleschick , W. A. , Pirrung , M. C. and Sohn , J. E. 1980 . J. Org. Chem. , 45 : 1066 Alternatively, Ketone 2 was prepared in 75% yield from acetone through addition of EtMgBr to trimethylsilylated acetocyano-hydrin followed acid hydrolysis and silylation with bis (trimethylsilyl)acetamide.
  • Masamune , S. , Ali , S. A. , Snitman , D. L. and Garvey , D. S. 1980 . Angew. Chem. Int. Ed. Engl. , 19 : 557 The stereoconfiguration is classified as syn and anti according to
  • Heathcock , C. H. , Pirrung , M. C. and Sohn , J. E. 1979 . J. Org. Chem. , 44 : 4294
  • Heathcock , C. H. , Young , S. D. , Hagen , J. P. , Pilli , R. and Badertscher , V. 1985 . J. Org. Chem. , 50 : 2095

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