Stereoselective construction of the tetracyclic scalarane skeleton from carvone

Chemical Communications

Volumn , Issue 5, 1999, Pages 427-428

  Abad, Antonio ^a   Agulló, Consuelo ^a   Cuñat, Ana C ^a   Llosá, M Carmen ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARVONE; SESTERTERPENE;

ARTICLE; CHEMICAL STRUCTURE; ISOMERISM; ORGANIC CHEMISTRY;

EID: 0033531413     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a900081j     Document Type: Article

References (22)

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19. For previous works which use carvone and an IMDA reaction for the construction of other polycyclic natural products, sec: V. H. Rawal and S. Iwasa, Abstracts of Papers, 204th National Meeting of the American Chemistry Society, Washington, DC, American Chemical Society, Washington, 1992, ORGN 35; T. K. M. Shing, Q. Jiang and T. C. W. Mak, J. Org. Chem., 1998, 63, 2056. For reviews of the intramolecular Diels - Alder reaction, see: W. R. Roush, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 5 (ed. L. A. Paquette), ch. 4.4, p. 513 and references cited therein.
20. For previous works which use carvone and an IMDA reaction for the construction of other polycyclic natural products, sec: V. H. Rawal and S. Iwasa, Abstracts of Papers, 204th National Meeting of the American Chemistry Society, Washington, DC, American Chemical Society, Washington, 1992, ORGN 35; T. K. M. Shing, Q. Jiang and T. C. W. Mak, J. Org. Chem., 1998, 63, 2056. For reviews of the intramolecular Diels - Alder reaction, see: W. R. Roush, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 5 (ed. L. A. Paquette), ch. 4.4, p. 513 and references cited therein.
21. For previous works which use carvone and an IMDA reaction for the construction of other polycyclic natural products, sec: V. H. Rawal and S. Iwasa, Abstracts of Papers, 204th National Meeting of the American Chemistry Society, Washington, DC, American Chemical Society, Washington, 1992, ORGN 35; T. K. M. Shing, Q. Jiang and T. C. W. Mak, J. Org. Chem., 1998, 63, 2056. For reviews of the intramolecular Diels - Alder reaction, see: W. R. Roush, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 5 (ed. L. A. Paquette), ch. 4.4, p. 513 and references cited therein.
22. A related strategy has been previously used for the synthesis of the AB rings of the labdane diterpene forskolin, see: M. I. Colombo, J. Zinezuk and E. A. Rúveda, Tetrahedron, 1992, 48, 963.