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(a) Arai, Y.; Hirohara, M.; Ogawa, R.; Masuda, K.; Shiojima, K.; Ageta, H.; Chang, H. C.; Chen, Y. P. Tetrahedron Lett. 1996, 37, 4381.
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Chen, Y.P.8
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(b) Akihisa, T.; Arai, K.; Kimura, Y.; Koike, K.; Kokke, W. C. M.; Shibata, T.; Nikaido, T. J. Nat. Prod. 1999, 62, 265.
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(c) Akihisa, T.; Koike, K.; Kimura, Y.; Sashida, N.; Matsumoto, T.; Ukiya, M.; Nikaido, T. Lipids 1999, 34, 1151.
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Nikaido, T.7
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(d) Roman, L. U.; Guerra-Ramirez, D.; Moran, G.; Martínez, I.; Hernández, J. D.; Cerda-Garcia-Rojas, C. M.; Torres-Valencia, J. M.; Joseph-Nathan, P. Org. Lett. 2004, 6, 173.
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Roman, L.U.1
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Torres-Valencia, J.M.7
Joseph-Nathan, P.8
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0037560988
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Although the biosynthesis of β-amyrin is known to proceed via 2,3-oxidosqualene, the fact that β-amyrin has been obtained after enzymatic cyclization of the 2,3-epoxide of racemic 1 should be also taken into account. Furthermore, oxidosqualene cyclase mutagenesis experiments, included those in which achilleol A and camelliol C are biosynthesized by mutant OSC, suggested that relatively few changes in the enzyme are needed to alter product specificity. These findings ultimately supported the existence of alternative pathways in the biosynthesis of terpenoids. For OCS mutagenesis experiments, see: (a) Segura, M. J. R.; Jackson, B. E.; Matsuda, S. P. T. Nat Prod. Rep. 2003, 20, 304.
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(b) Wendt, K. U.; Schulz, G. E.; Corey, E. J.; Liu, D. R. Angew. Chem. Int. Ed. 2000, 39, 2812.
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Wendt, K.U.1
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Liu, D.R.4
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0344623853
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(c) For biosynthesis of β-amyrin from the 2,3-epoxide of racemic 1, see: Horan, H.; McCormick, J. P.; Arigoni, D. J. Chem Soc., Chem. Commun. 1973, 3, 73.
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Horan, H.1
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Barrero, A. F.; Cuerva, J. M.; Alvarez-Manzaneda, E. J.; Oltra, E.; Chahboun, R. Tetrahedron Lett. 2002, 43, 2793.
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Barrero, A.F.1
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Chahboun, R.5
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11
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0035966238
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To our knowledge, only Theodorakis et al. have assayed the enantioselective variant of this reaction in their synthesis of (-)-acanthoic acid. Although the condensation reaction was attempted in the presence of different optically active catalysts, the highest ee obtained were of 60%: Ling, T.; Chowdhury, C.; Kramer, B. A.; Vong, B. G.; Palladino, M. A.; Theodorakis, E. A. J. Org. Chem. 2001, 66, 8843.
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Ling, T.1
Chowdhury, C.2
Kramer, B.A.3
Vong, B.G.4
Palladino, M.A.5
Theodorakis, E.A.6
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Van Tamalen, E. E.; Seiler, M. P.; Wierenga, W. J. Am. Chem. Soc. 1972, 94, 8229.
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Wierenga, W.3
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Ellis, J. E.; Dutcher, J. S.; Heathcock, C. H. J. Org. Chem. 1976, 41, 2670.
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14
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12044254693
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Reports by Barton and van Tamelen, showing that the use of different epimers in OSC-induced cyclizations, led to different results constituted an additional argument to pursue the enantioselective synthesis of these irregular triterpenes: Abe, I.; Rohmer, M.; Preswich, G. D. Chem. Rev. 1993, 93, 2189.
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Abe, I.1
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D'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymmetry 1992, 3, 459.
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Tetrahedron: Asymmetry
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16
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(a) Nazarov, I. N.; Zavyalov, S. I. Zh. Obshch. Khim. 1953, 23, 1703; Chem. Abstr. 1954, 48, 13667h.
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Zh. Obshch. Khim.
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Nazarov, I.N.1
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(a) Nazarov, I. N.; Zavyalov, S. I. Zh. Obshch. Khim. 1953, 23, 1703; Chem. Abstr. 1954, 48, 13667h.
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Chem. Abstr.
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19
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15944404124
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note
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+: 273.1467; found: 273.1463.
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20
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15944401902
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note
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1H NMR (800 MHz) spectroscopy, by integrating the AB quartets of the major and minor components.
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21
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0000833130
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Bertz, S. H.; Gibson, C. P.; Dabbagh, G. Tetrahedron Lett. 1987, 28, 4251.
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Tetrahedron Lett.
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Bertz, S.H.1
Gibson, C.P.2
Dabbagh, G.3
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22
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0001373616
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(a) (+)-α- and (+)-γ-polypodatetraenes have been isolated form the leaves of Polypodium and Polystichum species: Shiojima, K.; Arai, Y.; Masuda, K.; Kamada, T.; Ageta, H. Tetrahedron Lett. 1983, 24, 5733.
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(1983)
Tetrahedron Lett.
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Shiojima, K.1
Arai, Y.2
Masuda, K.3
Kamada, T.4
Ageta, H.5
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23
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0036637573
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(b) Although recently both polypodatetraenes have been reported from (-)-albicanol and (-)-drimenol by Akita et al., the method used by these authors supposed an elongation of the carbon chain of the sesquiterpenic precursors, as a previous step to the key C-20+C-10 coupling process: Kirosita, M.; Ohtsuka, M.; Nakamura, O.; Akita, H. Chem. Pharm. Bull. 2002, 50, 930.
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Chem. Pharm. Bull.
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Kirosita, M.1
Ohtsuka, M.2
Nakamura, O.3
Akita, H.4
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24
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0010221843
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Van Tamalen, E. E.; Hopla, R. E.; Kont, W. E. J. Am. Chem. Soc. 1979, 101, 6112.
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Van Tamalen, E.E.1
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