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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 12, 1982 - Issue 13
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Original Articles

On the Dual Mode of Aldol Cyclization of Bicyclo-[4.3.1] Decane-3,8-Dione: A Novel, Efficient Entry into the Isotwistanone System

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Pages 1039-1046 | Published online: 06 Dec 2006

References

  • Yamamoto , H. and Sham , H. L. 1979 . J. Am. Chem. Soc. , 101 : 1609 Syntheses of isocyanopupukeanane E. J. Corey and M. Ishiguro, Tetrahedron Lett., 1979, 2745.
  • Begley , M. J. , Mellor , M. and Pattenden , G. 1979 . J. Chem. Soc. Chem. Commun. , : 235
  • Alford , J. R. and McKervey , M. A. 1970 . J. Chem. Soc. Chem. Commun. , : 615
  • Stetter , S. and Lennartz , J. 1977 . Liebigs Ann. Chem. , : 1807 The structure of the starting amino alcohol was revised by the original authors
  • Momose , T. , Muraoka , O. and Atarashi , S. 1979 . Heterocycles , 12 : 37
  • Mp. 301–304°. Reported: mp 302–304°; see ref. 3.
  • Wide range of the melting point observed was caused by the concomitant isomer formation derived from the thermal equilibration between 8 and 9 on heating in a melting point apparatus. The melt was shown to be a mixture of 8 and 9 with predominance of the former on the basis of the 13C-NMR measurement.
  • Momose , T. and Muraoka , O. 1978 . Chem. Pharm. Bull. (Tokyo) , 26 : 2217
  • Cima , F. D. and Pietra , F. 1974 . J. Chem. Soc. Perkin I , : 1710
  • Hartman , M. 1966 . Z. Chem. , 6 : 182 S. Landa, J. Triska, M. Hajek, and P. Trska, Tetrahedron, 30, 4239 (1974)
  • Mp. 104–105°, IR(KBr) 3355, 3300cm−1, MS m/e 169 (M+, 8%), 139 (100%); 1H-NMR (CDCl3) δ1. 35–1.96 (12H, m, C3, 4, 6, 7, 8, 9-H), 1.96–2.30 (2H, m, C1 5-H), 2.78 (2H, s, -CH2N), 2.20 (3H, bs, OH & NH2)

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