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Many of the new synthetic hybrids show promising activity, see for example: P. Camps, R. El Achab, J. Morral, D. Muñoz-Torrero, A. Badia, J. E. Baños, N. M. Vivas, X. Barril, M. Orozco, F. J. Luque, J. Med. Chem. 2000, 43, 4657-4666.
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De La Torre, M.C.1
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For an overview of this field see: a) R. Dagani, Chem. Eng. News 2002, 80, 23-29;
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Melikyan, G.G.1
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(Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford
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b) A. J. M. Caffyn, K. M. Nicholas in Comprehensive Organometallic Chemistry II, Vol 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 685-702.
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Angew. Chem. Int. Ed. 2000, 39, 1538-1559;
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M. C. de la Torre, I. García, M. A. Sierra, Tetrahedron Lett. 2002, 43, 6351-6353.
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M. C. de la Torre, I. García, M. A. Sierra, J. Nat. Prod. 2002, 65, 661-668.
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0032548961
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For terpenes having a structure related to 10 see for example: a) P. A. Zoretic, H. Fang, A. A. Ribeiro, G. Dubay, J. Org. Chem. 1998, 63, 1156-1161;
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b) I.-S. Lee, X. Ma, H.-B. Chai, D. A. Madulid, R. B. Lamont, M. J. O'Neill, J. M. Besterman, N. R. Farnworth, D. D. Soejarto, G. A. Cordell, Tetrahedron 1995, 51, 21-28;
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c) P. Martres, P. Perfetti, J. P. Zahra, B. Waegell, Tetrahedron Lett. 1993, 34, 3127-3128;
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d) A. F. Barrero, J. F. Sánchez, E. J. Alvarez-Manzaneda, J. Altarejos, M. Muñoz, A. Haïdour, Tetrahedron 1994, 50, 6653-6662.
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25
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0001049265
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Interestingly, a tricyclic diterpenoid analogue, related to 9 was obtained as minor reaction product (8%) in the cationically induced cyclization of 14-hydroxylabdadiene, see: P. Sundararaman, W. Hertz, J. Org. Chem. 1977, 42, 806-813.
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0004205843
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Chapman and Hall, London
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For clarity, the numbering systems given here for the natural fragments are the most commonly used, see: J. D. Connoly, R. A. Hill, Dictionary of Terpenoids, Vol. 1, Chapman and Hall, London, 1991.
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a) A. K. Saksena, M. J. Green, P. Mangiaracina, J. K. Wong, W. Kreutner, A. R. Gulbenkian, Tetrahedron Lett. 1985, 26, 6423-6426;
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a) P. Magnus, S. A. Eisenbeis, R. A. Fairhurst, T. Iliadis, N. A. Magnus, D. Parry, J. Am. Chem. Soc. 1997, 119, 5591-5605;
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32
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0011467334
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Some examples of α→β pinene isomerization are: a) G. Déléris, J. Kowalsky, J. Dunoguès, R. Calas, Tetrahedron Lett. 1977, 18, 4211-4214;
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Calas, R.4
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36
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33748319952
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note
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2-alkyne complex has been found. The theoretical study of the mechanism of these and related processes fall out the scope of this paper and will be reported in due time.
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37
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0002015317
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a) G. Savona, M. Paternostro, F. Piozzi, B. Rodríguez, Tetrahedron Lett. 1979, 20, 379-382;
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b) P. Y. Malakov, G. Y. Papanov, I. M. Boneva, Phytochemistry 1992, 31, 4029-4030;
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Malakov, P.Y.1
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c) M. Bruno, C. Fazio, F. Piozzi, B. Rodríguez, M. C. de la Torre, Phytochemistry 1995, 40, 1481-1483.
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33748318398
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a) C. Djerassi, M. Gorman, A. L. Nussbaum, J. Reynoso, J. Am. Chem. Soc. 1953, 75, 5446-5447;
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33748311124
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b) C. Djerassi, M. Gorman, A. L. Nussbaum, J. Reynoso, J. Am. Chem. Soc. 1954, 76, 4463-4465;
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43
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G. Domínguez, M. C. de la Torre, B. Rodríguez, J. Org. Chem. 1991, 56, 6595-6600.
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44
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33748294757
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note
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These compounds were isolated from a very complex reaction mixture, which exhibited the presence of unknown decomposition products.
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45
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33748322291
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note
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2 complexes formed from 12 and 13 to steric effects. This property warrants a total stereoselectivity around the newly formed double bond as well as the control of the regiochemistry.
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