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(a) Kodama, M.; Shimada, K.; Takahashi, T.; Kabuto, C.; Itô, S. Tetrahedron Lett. 1981, 22, 4271.
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0028815422
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(a) Piet, D. P.; Minnaard, A. J.; van der Heijden, K. A.; Franssen, M. C. R.; Wijnberg, J. B. P. A.; de Groot, A. Tetrahedron 1995, 51, 243.
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(b) Piet, D. P.; Schrijvers, R.; Franssen, M. C. R.; de Groot, A. Tetrahedron 1995, 51, 6303.
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17
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0013536833
-
-
The fragmentation has also been used for the synthesis of (±)- and (+)-hedycaryol, see: (b) Wharton, P. S.; Sundin, C. E.; Johnson, D. W.; Kluender, H. C. J. Org. Chem. 1972, 37, 34 and (c) Minnaard, A. J.; Wijnberg, J. B. P. A.; de Groot, A. Tetrahedron 1994, 50, 4755, respectively.
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18
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0028232283
-
-
The fragmentation has also been used for the synthesis of (±)- and (+)-hedycaryol, see: (b) Wharton, P. S.; Sundin, C. E.; Johnson, D. W.; Kluender, H. C. J. Org. Chem. 1972, 37, 34 and (c) Minnaard, A. J.; Wijnberg, J. B. P. A.; de Groot, A. Tetrahedron 1994, 50, 4755, respectively.
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Minnaard, A.J.1
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De Groot, A.3
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19
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15844380762
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-
note
-
The numbering system as given in structure 4 will be followed throughout the text of this paper.
-
-
-
-
20
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15844385096
-
-
Chapman & Hall: London, Mono- and Sesquiterpenoids
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Connolly, J. D.; Hill, R. A. Dictionary of Terpenoids; Chapman & Hall: London, 1991; Vol. 1, Mono- and Sesquiterpenoids, p 326.
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Connolly, J.D.1
Hill, R.A.2
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21
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0003824820
-
-
Wiley Interscience: New York
-
For some representative examples, see: (a) Ho, T.-L. Enantioselective Synthesis, Natural Products from Chiral Terpenes; Wiley Interscience: New York, 1992; pp 132-135. (b) Li, Y.; Chen, X.; Shao, S.; Li, T. Synth. Commun. 1993, 23, 2457. (c) Liu, L.; Xiong, Z.; Nan, F.; Li, T.; Li, Y. Bull. Soc. Chim. Belg. 1995, 104, 73.
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Ho, T.-L.1
-
22
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0027219760
-
-
For some representative examples, see: (a) Ho, T.-L. Enantioselective Synthesis, Natural Products from Chiral Terpenes; Wiley Interscience: New York, 1992; pp 132-135. (b) Li, Y.; Chen, X.; Shao, S.; Li, T. Synth. Commun. 1993, 23, 2457. (c) Liu, L.; Xiong, Z.; Nan, F.; Li, T.; Li, Y. Bull. Soc. Chim. Belg. 1995, 104, 73.
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Li, Y.1
Chen, X.2
Shao, S.3
Li, T.4
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23
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-
84988090419
-
-
For some representative examples, see: (a) Ho, T.-L. Enantioselective Synthesis, Natural Products from Chiral Terpenes; Wiley Interscience: New York, 1992; pp 132-135. (b) Li, Y.; Chen, X.; Shao, S.; Li, T. Synth. Commun. 1993, 23, 2457. (c) Liu, L.; Xiong, Z.; Nan, F.; Li, T.; Li, Y. Bull. Soc. Chim. Belg. 1995, 104, 73.
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Liu, L.1
Xiong, Z.2
Nan, F.3
Li, T.4
Li, Y.5
-
25
-
-
15844396995
-
-
Reference 15a, pp 198-200 and 272-273.
-
(a) Reference 15a, pp 198-200 and 272-273.
-
-
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26
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0026529512
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(b) Haaksma, A. A.; Jansen, B. J. M.; de Groot, A. Tetrahedron 1992, 48, 3121.
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Haaksma, A.A.1
Jansen, B.J.M.2
De Groot, A.3
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27
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0027403311
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(c) Agami, C.; Kadouri-Puchot, C.; Le Guen, V. Tetrahedron: Asymm. 1993, 4, 641.
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Agami, C.1
Kadouri-Puchot, C.2
Le Guen, V.3
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28
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0027404925
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Tenius, B. S. M.; de Oliveira, E. R.; Ferraz, H. M. C. Tetrahedron: Asymm. 1993, 4, 633.
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De Oliveira, E.R.2
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(a) Pfau, M.; Revial, G.; Guingant, A.; d'Angelo, J. J. Am. Chem. Soc. 1985, 107, 273.
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0026561424
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Review: (b) d'Angelo, J.; Desmaële, D.; Dumas, F.; Guingant, A. Tetrahedron: Asymm. 1992, 3, 459.
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D'Angelo, J.1
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0002842156
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The well-described procedure was followed: Revial, G.; Pfau, M. Org. Synth. 1992, 70, 35.
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Revial, G.1
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32
-
-
15844364772
-
-
note
-
The use of (S)-(-)-1-phenylethylamine resulted in a selective formation of (-)-10-epi-α-cyperone in 67% overall yield from (+)-dihydrocarvone.
-
-
-
-
34
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0038539532
-
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Ando, M.; Akahane, A.; Takase, K. Bull. Chem. Soc. Jpn. 1978, 57, 283.
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35
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0004157026
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Trost, B. M., Ed.; Blackwell Science: London
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(a) Narasaka, K. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed.; Blackwell Science: London, 1994; pp 17-36.
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Narasaka, K.1
-
38
-
-
15844429153
-
-
note
-
2 gave selectively the corresponding α epoxide.
-
-
-
-
39
-
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0000970435
-
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Zoretic, P. A.; Chambers, R. J.; Marbury, G. D.; Riebiro, A. A. J. Org. Chem. 1985, 50, 2981.
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Chambers, R.J.2
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Riebiro, A.A.4
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40
-
-
49349139760
-
-
It was expected that ring opening of the side-chain epoxide in 12 would occur during the formation of the allylic selenide. For example, see: Clive, D. L. J. Tetrahedron 1978, 34, 1049.
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(1978)
Tetrahedron
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Clive, D.L.J.1
-
41
-
-
0000668550
-
-
The epoxidation of olefinic bonds, probably due to the formation of arylperoxyseleninic acid, is a known problem in the selenoxide chemistry, see: (a) Grieco, P. A.; Yokoyama, Y.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1977, 42, 2034. (b) Hori, T.; Sharpless, K. B. J. Org. Chem. 1978, 43, 1689.
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Grieco, P.A.1
Yokoyama, Y.2
Gilman, S.3
Nishizawa, M.4
-
42
-
-
33947092633
-
-
The epoxidation of olefinic bonds, probably due to the formation of arylperoxyseleninic acid, is a known problem in the selenoxide chemistry, see: (a) Grieco, P. A.; Yokoyama, Y.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1977, 42, 2034. (b) Hori, T.; Sharpless, K. B. J. Org. Chem. 1978, 43, 1689.
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Hori, T.1
Sharpless, K.B.2
-
43
-
-
15844362110
-
-
note
-
28
-
-
-
-
44
-
-
0001652973
-
-
(a) Ireland, R. E.; Muchmore, D. C.; Hengartner, U. J. Am. Chem. Soc. 1972, 94, 5098.
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Ireland, R.E.1
Muchmore, D.C.2
Hengartner, U.3
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48
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0000540970
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Blay, G.; Cardona, L.; García, B.; Pedro, J. R. J. Org. Chem. 1993, 58, 7204.
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Blay, G.1
Cardona, L.2
García, B.3
Pedro, J.R.4
-
50
-
-
15844377851
-
-
note
-
We thank Prof. Dr. G. Appendino for supplying copies of the NMR spectra of natural allohedycaryol.
-
-
-
-
51
-
-
37049115186
-
-
The conventions proposed for describing germacrane sesquiterpenes are followed: Rogers, D.; Moss, G. P.; Neidle, S. J. Chem. Soc., Chem. Commun. 1972, 142.
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J. Chem. Soc., Chem. Commun.
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Rogers, D.1
Moss, G.P.2
Neidle, S.3
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52
-
-
15844382564
-
-
Prof. Dr. G. Appendino attended us to an article in which the isolation of α-ferulene, another ent-sesquiterpene from F. communis, has been reported: Carboni, S.; Da Settimo, A.; Malaguzzi, V.; Marsili, A; Pacini, P. L. Tetrahedron Lett. 1995, 3017.
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Tetrahedron Lett.
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-
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Carboni, S.1
Da Settimo, A.2
Malaguzzi, V.3
Marsili, A.4
Pacini, P.L.5
-
55
-
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15844403240
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(b) Neykov, G. D.; Ivanov, P. M.; Orahovats, A. S. J. Mol. Struct. 1987, 153, 147.
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Neykov, G.D.1
Ivanov, P.M.2
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-
57
-
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15844363636
-
-
Reference 14, p 636
-
Reference 14, p 636.
-
-
-
-
59
-
-
15844400676
-
-
note
-
15c,17b
-
-
-
-
60
-
-
15844429906
-
-
note
-
1H NMR (main peaks) δ 2.49-2.61 (m, 2 H), 3.82 (dd, J = 5.1, 3.6 Hz, 1 H), 5.22-5.52 (m, 2 H), 5.72 (m, 1 H)].
-
-
-
-
61
-
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15844423636
-
-
note
-
46 yielded 16 in 95%.
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-
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