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1
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(a) Fujioka, H.; Kitagaki, S.; Imai, R.; Kondo, M.; Okamoto, S.; Yoshida, Y.; Akai, S.; Kita, Y. Tetrahedron Lett. 1995, 36, 3219-3222.
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Fujioka, H.1
Kitagaki, S.2
Imai, R.3
Kondo, M.4
Okamoto, S.5
Yoshida, Y.6
Akai, S.7
Kita, Y.8
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2
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0031562092
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(b) Kita, Y.; Kitagaki, S.; Yoshida, Y.; Mihara, S.; Fang, D.-F.; Fujioka, H. Tetrahedron Lett. 1997, 38, 1061-1064.
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Kita, Y.1
Kitagaki, S.2
Yoshida, Y.3
Mihara, S.4
Fang, D.-F.5
Fujioka, H.6
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3
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8544276578
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(c) Kita, Y.; Kitagaki, S.; Yoshida, Y.; Mihara, S.; Fang, D.-F.; Kondo, M.; Okamoto, S.; Imai, R.; Akai, S.; Fujioka, H. J. Org. Chem. 1997, 62, 4991-4997.
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Kita, Y.1
Kitagaki, S.2
Yoshida, Y.3
Mihara, S.4
Fang, D.-F.5
Kondo, M.6
Okamoto, S.7
Imai, R.8
Akai, S.9
Fujioka, H.10
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4
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0033574681
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(d) Kita, Y.; Yoshida, Y.; Kitagaki, S.; Mihara, S.; Fang, D.-F.; Furukawa, A.; Higuchi, K.; Fujioka, H. Tetrahedron 1999, 55, 4979-4998.
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(1999)
Tetrahedron
, vol.55
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Kita, Y.1
Yoshida, Y.2
Kitagaki, S.3
Mihara, S.4
Fang, D.-F.5
Furukawa, A.6
Higuchi, K.7
Fujioka, H.8
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5
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0035966223
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Kita, Y.; Furukawa, A.; Futamura, J.; Ueda, K.; Sawama, Y.; Hamamoto, H.; Fujioka, H. J. Org. Chem. 2001, 66, 8779-8786.
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J. Org. Chem.
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Kita, Y.1
Furukawa, A.2
Futamura, J.3
Ueda, K.4
Sawama, Y.5
Hamamoto, H.6
Fujioka, H.7
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6
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0029937840
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(a) Kita, K.; Kitagaki, S.; Imai, R.; Okamoto, S.; Mihara, S.; Yoshida, Y.; Akai, S.; Fujioka, H. Tetrahedron Lett. 1996, 37, 1817-1820.
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(1996)
Tetrahedron Lett.
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, pp. 1817-1820
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Kita, K.1
Kitagaki, S.2
Imai, R.3
Okamoto, S.4
Mihara, S.5
Yoshida, Y.6
Akai, S.7
Fujioka, H.8
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7
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0034719737
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(b) Kita, Y.; Furukawa, A.; Futamura, J.; Higuchi, K.; Ueda, K.; Fujioka, H. Tetrahedron Lett. 2000, 41, 2133-2136. Quite recently we found that the reaction of acyclic 2-aryl-2,3-epoxy acylates proceeded via the C3-cleavage of the oxirane ring. However, the intermediates are phenonium ions, which are completely different from the intermediates of eqs 1 and 2 due to the flexibility of the substrates. Kita, Y.; Furukawa, A.; Futamura, J.; Higuchi, K.; Ueda, K.; Fujioka, H. Tetrahedron 2001, 57, 815-825.
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Tetrahedron Lett.
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Kita, Y.1
Furukawa, A.2
Futamura, J.3
Higuchi, K.4
Ueda, K.5
Fujioka, H.6
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8
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0035961113
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(b) Kita, Y.; Furukawa, A.; Futamura, J.; Higuchi, K.; Ueda, K.; Fujioka, H. Tetrahedron Lett. 2000, 41, 2133-2136. Quite recently we found that the reaction of acyclic 2-aryl-2,3-epoxy acylates proceeded via the C3-cleavage of the oxirane ring. However, the intermediates are phenonium ions, which are completely different from the intermediates of eqs 1 and 2 due to the flexibility of the substrates. Kita, Y.; Furukawa, A.; Futamura, J.; Higuchi, K.; Ueda, K.; Fujioka, H. Tetrahedron 2001, 57, 815-825.
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(2001)
Tetrahedron
, vol.57
, pp. 815-825
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Kita, Y.1
Furukawa, A.2
Futamura, J.3
Higuchi, K.4
Ueda, K.5
Fujioka, H.6
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9
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0037421024
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We have recently reported the asymmetric synthesis of (-)-herbertenediol through the rearrangement of 3-aryl-2-methyl-2,3-epoxy tosylate. See: Kita, Y.; Futamura, J.; Ohba, Y.; Sawama, Y.; Ganesh, J. K.; Fujioka, H. Tetrahedron Lett. 2003, 44, 411-413.
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(2003)
Tetrahedron Lett.
, vol.44
, pp. 411-413
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Kita, Y.1
Futamura, J.2
Ohba, Y.3
Sawama, Y.4
Ganesh, J.K.5
Fujioka, H.6
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10
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0038271016
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note
-
In this section, racemic epoxysulfonates were used to examine their reactivity under Lewis acid treatment.
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11
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0038271017
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note
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The reaction mechanism for compounds 3 and 4 will be discussed elsewhere.
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12
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1542635938
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3Al, see: (a) Ishihara, K.; Hanaki, N.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 7074-7075.
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(1991)
J. Am. Chem. Soc.
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Ishihara, K.1
Hanaki, N.2
Yamamoto, H.3
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14
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0001647878
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Gulavita, N.; Hori, A.; Shimizu, Y.; Laszlo, P.; Clardy, J. Tetrahedron Lett. 1988, 29, 4381-4384.
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(1988)
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Gulavita, N.1
Hori, A.2
Shimizu, Y.3
Laszlo, P.4
Clardy, J.5
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15
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0025365543
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Takano, S.; Inomata, K.; Sato, T.; Takahashi, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1990, 290-292.
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Takano, S.1
Inomata, K.2
Sato, T.3
Takahashi, M.4
Ogasawara, K.5
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16
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0000118162
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(a) Shiotani, S.; Okada, H.; Nakamura, K.; Yamamoto, T.; Sekino, F. Heterocycles 1996, 43, 1031-1047.
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Heterocycles
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Shiotani, S.1
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Yamamoto, T.4
Sekino, F.5
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17
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0011882244
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(b) Shimizu, M.; Kamikubo, T.; Ogasawara, K. Heterocycles 1997, 44, 21-26.
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Heterocycles
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Shimizu, M.1
Kamikubo, T.2
Ogasawara, K.3
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18
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0024431880
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Asymmetric synthesis of unnatural (+)-aphanorphine, see: Takano, S.; Inomata, K.; Sato, T.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 1591-1592.
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(1989)
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Takano, S.1
Inomata, K.2
Sato, T.3
Ogasawara, K.4
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19
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0035808867
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For formal sythesis of (-)-aphanorphine, see: (a) Tanaka, K.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2001, 42, 1049-1052.
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Tanaka, K.1
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Ogasawara, K.3
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(d) Hulme, A. N.; Henry, S. S.; Meyers, A. I. J. Org. Chem. 1995, 60, 1265-1270.
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Hulme, A.N.1
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24
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0007906819
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(f) Node, M.; Imazato, H.; Kurosaki, R.; Kawano, Y.; Inoue, T.; Nishide, K.; Fuji, K. Heterocycles 1996, 42, 811-819.
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Node, M.1
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Nishide, K.6
Fuji, K.7
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33845282438
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Corey, E. J.; Bakshi, R. K.; Shibata. S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926. The absolute configuration of the secondary alcohol was deduced by referring to the literature and our previous study (refs 1-3). This deduction was consequently determined by agreement of the synthesized 10 to the authentic one.
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Corey, E.J.1
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(e) Irita, H.; Hashimoto, T.; Fukuyama, Y.; Asakawa, Y. Phytochemistry 2000, 55, 247-253.
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Irita, H.1
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Asakawa, Y.4
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33
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0037933610
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note
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For racemic synthesis, see ref 21f and references therein.
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34
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0033525851
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For asymmetric synthesis, see: Adad, A.; Agulló, C.; Cuñat, A. C.; Perni, R. H. J. Org. Chem. 1999, 64, 1741-1744 and ref 20d.
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J. Org. Chem.
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Adad, A.1
Agulló, C.2
Cuñat, A.C.3
Perni, R.H.4
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0033556227
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(a) Bringmann, G.; Pabst, T.; Rycroft, D. S.; Connolly, J. D. Tetrahedron Lett. 1999, 40, 483-486.
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Bringmann, G.1
Pabst, T.2
Rycroft, D.S.3
Connolly, J.D.4
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38
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0034721428
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(c) Bringmann, G.; Pabst, T.; Henschel, P.; Kraus, J.; Peters, K.; Peters, E. M.; Rycroft, D. S.; Connolly, J. D. J. Am. Chem. Soc. 2000, 122, 9127-9133.
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Bringmann, G.1
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Peters, K.5
Peters, E.M.6
Rycroft, D.S.7
Connolly, J.D.8
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39
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0035855316
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(d) Fukuyama, Y.; Matsumoto, K.; Tonoi, Y.; Yokoyama, R.; Takahashi, H.; Minami, H.; Okazaki, H.; Mitsumoto, Y. Tetrahedron 2001, 57, 7127-7135.
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Tetrahedron
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Fukuyama, Y.1
Matsumoto, K.2
Tonoi, Y.3
Yokoyama, R.4
Takahashi, H.5
Minami, H.6
Okazaki, H.7
Mitsumoto, Y.8
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40
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0030020250
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(a) Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1996, 37, 1261-1264.
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Fukuyama, Y.1
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85047695774
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(c) Gupta, P. D.; Pal, A.; Roy, A.; Mukherjee, D. Tetrahedron Lett. 2000, 41, 7563-7566.
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Gupta, P.D.1
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0035955790
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(e) Abad, A.; Agulló, C.; Cuñat, A. C.; Jiménez, D.; Perni, R. H. Tetrahedron 2001, 57, 9727-9735.
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Abad, A.1
Agulló, C.2
Cuñat, A.C.3
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Perni, R.H.5
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Reetz, M.T.1
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49
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0035961113
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The same tendency in the formation of the phenonium ion intermediate, i.e., the difference between the cyclic system not forming the phenonium ion and the acyclic system forming the phenonium ion, was observed in our previous study; see: Kita, Y.; Furukawa, A.; Futamura, J.; Higuchi, K.; Ueda, K.; Fujioka, H. Tetrahedron 2001, 57, 815-825.
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(2001)
Tetrahedron
, vol.57
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Kita, Y.1
Furukawa, A.2
Futamura, J.3
Higuchi, K.4
Ueda, K.5
Fujioka, H.6
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50
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33947087514
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Burgess, E. M.; Penton, H. R., Jr.; Taylor, E. A. J. Org. Chem. 1973, 38, 26-31. For a successful result, see: Kita, Y.; Higuchi, K.; Yoshida, Y.; Iio, K.; Kitagaki, S.; Ueda, K.; Akai, S.; Fujioka, H. J. Am. Chem. Soc. 2001, 123, 3214-3222.
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Burgess, E.M.1
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51
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0034829733
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Burgess, E. M.; Penton, H. R., Jr.; Taylor, E. A. J. Org. Chem. 1973, 38, 26-31. For a successful result, see: Kita, Y.; Higuchi, K.; Yoshida, Y.; Iio, K.; Kitagaki, S.; Ueda, K.; Akai, S.; Fujioka, H. J. Am. Chem. Soc. 2001, 123, 3214-3222.
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Kita, Y.1
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Ueda, K.6
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Nishimura, J.3
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