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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 7, 1977 - Issue 5
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Original Articles

Synthesis of Terpenoids. IV. The Use of Kinetic Enolates of some Methyl Ketones For Terpenoid Syntheses

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Pages 345-350 | Received 20 Apr 1977, Published online: 23 Oct 2006

References

  • 1975 . A portion of this work constitutes part of the thesis presented by O. S. P. to División de Estudios Superiores de la Facultad de Química, UNAM, in partial fulfillment for her Ph.D. degree (june.
  • Stork , G. , Kraus , G. A. and García , G. A. 1974 . J. Org. Chem. , 39 : 3459 M. Gaudemar, Compt. Rend. (c), 279, 961 (1974); I. Kuwajima, T. Sato, M. Arai and N. Minami, Tetrahedron Letters—1817 (1976).
  • Denniff , P. and Whiting , D. A. 1976 . Chem. Comm. , : 712 See for instance:.
  • Manjarrez , A. , Rios , T. and Guzmán , A. 1964 . Tetrahedron , 20 : 333
  • Bohlman , F. and Rao , N. 1972 . Tetrahedron Lett. , : 1295
  • Malanco , F. L. and Maldonado , L. A. 1976 . Synthetic Comm. , 6 : 515 a) -(;
  • Gopichand , Y. and Chakravarti , K. K. 1974 . Tetrahedron Lett. , : 3851
  • One step routes to α-trans-atlantone and deodarone from synthetic α-bisabololone have been described6a,6b
  • Ho , T-L. 1974 . Synthetic Comm. , 4 : 189 a);
  • Banno , K. 1976 . Bull. Chem. Soc. Japan , 49 : 2284 and references cited therein;
  • unpublished results of this laboratories.
  • Adams , D. R. , Bhatnagar , S. P. , Cookson , R. C. and Tuddenham , R. M. 1974 . Tetrahedron Lett. , : 3197 a);
  • Garbers , C. F. and Scott , F. Tetrahedron Lett. , 1625 and references cited therein.
  • 8a and references cited therein.
  • We were unable to obtain ar-turmerone by direct reaction of 1a with bromide 5.
  • The synthetic sample was contaminated with about 6% of another compound which showed a singlet at 1.05 ppm suggesting the presence of t-butyl groups. However its full characterization has not been attempted.
  • Colorless oil; uv λmax (MeOH) 241 nm (ε 12160); ir (film) 3420, 1675, 1620, 990, 920 cm−1; nmr (CDCl3) [stilde] 1.30, 1.91 and 2.15 (s, 3H each), 2.70 (AB system, J=18Hz, 2H), 4.40 (broad signal, OH), 4.96 (dd, J=10Hz, J=2Hz, 1H), 5.20 (dd, J=16Hz, J=2Hz, 1H), 5.96 (dd, J=16Hz, J=10Hz, 1H), 6.03 (s, 1H).
  • Calderón , J. , Muñoz , J. L. , Quijano , L. and Ríos , T. 1976 . Rev. Latinoamer. Quím. , 7 : 114 have reported the isolation of ocimenones from tagetes species.
  • Colorless oil; ir (film) 3450, 1710, 990, 910 cm−1; nmr (CDCl3) δ 0.90 (d, J=6Hz, 6H), 1.26 (s, 3H), 1.93 (m, 1H), 2.26 (s, 2H), 2.26 (AB system, J=16Hz, 2H), 4.23 (broad s, OH), 5.00 (dd, - J=11Hz, J=2Hz, 1H), 5.20 (dd, J=18Hz, J=2Hz, 1H), 5.95 (dd, - J=18Hz, J=11Hz, 1H).
  • Sook Park , Oee and Maldonado , L. A. acknowledge Cámara Nacional de la Industria de Laboratorios Químico Farmacéuticos for partial support of their work.

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