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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 1
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Original Articles

Synthesis of the Himachalenes by an Intramolecular Diels-Alder Reaction Route

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Pages 45-48 | Received 13 Nov 1972, Published online: 06 Dec 2006

References

  • 1970–1971 . Postdoctoral fellow
  • Klemm , L. H. and Santhanam , P. S. 1972 . J. Het. Chem. , 9 : 423 Prior to the present work only syntheses of podophylloid substances employed the scheme [, and earlier references; E. Block and R. Stevenson, J. Org. Chem. 36, 3453 (1971)]. In the meantime1 other syntheses appeared [W. Oppolzer and K. Keller, J. Amer. Chem. Soc. 93, 3836 (1971); N. Fukamiya, M. Kato, and A. Yoshikoshi, Chem. Comm., 1120 (1971)]
  • Challand , B. D. , Kornis , G. , Lange , G. L. and de Mayo , P. 1967 . Chem. Comm. , : 704 For their previous synthesis see
  • Wenkert , E. and Gaoni , Y. 1966 . J. Org. Chem. , 31 : 3809
  • Thomas , A. F. and Pawlak , W. 1971 . Helv. Chim. Acta , 54 : 1822 For photooxygenations of olefins related to 4, reported since completion of the present work, see
  • Ratcliffe , R. and Rodehorst , R. 1970 . J. Org. Chem. , 35 : 4000
  • Thompson , H. W. and Melillo , D. G. 1970 . J. Amer. Chem. Soc. , 92 : 3218 The Diels-Alder reaction was modelled after the reactions of butadienes and cyclohexenones induced by aluminum chloride which in a broad study during 1967–1970 (E. Wenkert and C. A. Michalsky, unpublished data) had been shown to produce octalinones in high yield; cf. also
  • Joseph , T. C. and Dev , S. 1968 . Tetrahedron , 24 : 3853 Base-induced equilibration of 11 gave a ca. 1:1 mixture of 11 and its known trans isomer
  • Bisarya , S. C. and Dev , S. 1968 . Tetrahedron , 24 : 3861 For himachalol see
  • Bredenberg , J. B-son and Erdtman , H. 1961 . Acta Chim. Scand. , 15 : 685 T. C. Joseph and S. Dev, Tetrahedron 24, 3809, 3841 (1968)
  • This was furnished kindly by Professors H. Erdtman and T. Norin

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