-
1
-
-
8244237605
-
-
The numbering system as given in structure 1 will be followed throughout the text of this paper
-
The numbering system as given in structure 1 will be followed throughout the text of this paper.
-
-
-
-
2
-
-
0342982496
-
-
Towers, G. H. N., Stafford, H. A., Eds.; Plenum Press: New York; Chapter 4
-
(a) Fischer, N. H. In Recent Advances in Phytochemistry, Vol. 24: Biochemistry of the Mevalonic Acid Pathway to Terpenoids; Towers, G. H. N., Stafford, H. A., Eds.; Plenum Press: New York, 1990; Chapter 4.
-
(1990)
Recent Advances in Phytochemistry, Vol. 24: Biochemistry of the Mevalonic Acid Pathway to Terpenoids
, vol.24
-
-
Fischer, N.H.1
-
3
-
-
84988074896
-
-
and references cited therein
-
(b) Marco, J. A.; Sanz-Cervera, J. F.; García-Lliso, V.; Domingo, L. R.; Carda, M.; Rodríguez, S.; López-Ortiz, F.; Lex, J. Liebigs Ann. Chem. 1995, 1837 and references cited therein.
-
(1995)
Liebigs Ann. Chem.
, pp. 1837
-
-
Marco, J.A.1
Sanz-Cervera, J.F.2
García-Lliso, V.3
Domingo, L.R.4
Carda, M.5
Rodríguez, S.6
López-Ortiz, F.7
Lex, J.8
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4
-
-
0028815422
-
-
Piet, D. P.; Minnaard, A. J.; van der Heyden, K. A.; Franssen, M. C. R.; Wijnberg, J. B. P. A.; de Groot, A. Tetrahedron 1995, 51, 243.
-
(1995)
Tetrahedron
, vol.51
, pp. 243
-
-
Piet, D.P.1
Minnaard, A.J.2
Van Der Heyden, K.A.3
Franssen, M.C.R.4
Wijnberg, J.B.P.A.5
De Groot, A.6
-
6
-
-
0003177544
-
-
(a) Wharton, P. S.; Poon, Y. C.; Kluender, H. C. J. Org. Chem. 1973, 38, 735.
-
(1973)
J. Org. Chem.
, vol.38
, pp. 735
-
-
Wharton, P.S.1
Poon, Y.C.2
Kluender, H.C.3
-
9
-
-
0004205843
-
-
Chapman & Hall: London, Mono- and Sesquiterpenoids
-
(a) Connolly, J. D.; Hill, R. A. Dictionary of Terpenoids; Chapman & Hall: London, 1991; Vol. 1, Mono- and Sesquiterpenoids.
-
(1991)
Dictionary of Terpenoids
, vol.1
-
-
Connolly, J.D.1
Hill, R.A.2
-
11
-
-
0001026716
-
-
The 7-epi-eudesmanes are the antipodes of 5-epi-10-epi-eudesmanes and, consequently, possess the ent-configuration. For example, see: van Beek, T. A.; Kleis, R.; Posthumus, M. A.; van Veldhuizen, A. Phytochemistry 1989, 28, 1909.
-
(1989)
Phytochemistry
, vol.28
, pp. 1909
-
-
Van Beek, T.A.1
Kleis, R.2
Posthumus, M.A.3
Van Veldhuizen, A.4
-
12
-
-
0027602015
-
-
For some representative examples, see: (a) Prudent, D.; Perineau, F.; Bessiere, J. M.; Michel, G.; Bravo, R. J. Essent. Oil Res. 1993, 5, 255. (b) Cañigueral, S.; Vila, R.; Vicario, G.; Tomas, X.; Adzet, T. Biochem. Syst. Ecol. 1994, 22, 307.
-
(1993)
J. Essent. Oil Res.
, vol.5
, pp. 255
-
-
Prudent, D.1
Perineau, F.2
Bessiere, J.M.3
Michel, G.4
Bravo, R.5
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13
-
-
0028140972
-
-
For some representative examples, see: (a) Prudent, D.; Perineau, F.; Bessiere, J. M.; Michel, G.; Bravo, R. J. Essent. Oil Res. 1993, 5, 255. (b) Cañigueral, S.; Vila, R.; Vicario, G.; Tomas, X.; Adzet, T. Biochem. Syst. Ecol. 1994, 22, 307.
-
(1994)
Biochem. Syst. Ecol.
, vol.22
, pp. 307
-
-
Cañigueral, S.1
Vila, R.2
Vicario, G.3
Tomas, X.4
Adzet, T.5
-
14
-
-
85022508846
-
-
Itokawa, H.; Morita, H.; Watanabe, K.; Mihoshi, S.; Iitaka, Y. Chem. Pharm. Bull. 1985, 33, 1148.
-
(1985)
Chem. Pharm. Bull.
, vol.33
, pp. 1148
-
-
Itokawa, H.1
Morita, H.2
Watanabe, K.3
Mihoshi, S.4
Iitaka, Y.5
-
15
-
-
8244240972
-
-
Kodama, M.; Shimada, K.; Itô, S. Tetrahedron Lett. 1981, 22, 1523.
-
(1981)
Tetrahedron Lett.
, vol.22
, pp. 1523
-
-
Kodama, M.1
Shimada, K.2
Itô, S.3
-
17
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-
0000992524
-
-
An indication for this pathway is the cooccurrence of trans,cis-farnesol (a precursor of cis,trans-germacranes) and epi-eudesmanes in Galbanum species, see: Thomas, A. F.; Ozainne, M. Helv. Chim. Acta 1978, 61, 2874.
-
(1978)
Helv. Chim. Acta
, vol.61
, pp. 2874
-
-
Thomas, A.F.1
Ozainne, M.2
-
18
-
-
0013559027
-
-
Kodama, M.; Yokoo, S.; Matsuki, Y.; Itô, S. Tetrahedron Lett. 1979, 1687.
-
(1979)
Tetrahedron Lett.
, pp. 1687
-
-
Kodama, M.1
Yokoo, S.2
Matsuki, Y.3
Itô, S.4
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19
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-
0013500096
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-
All trans,cis-germacranes (heliangolides) and cis,trans-germacranes (melampolides) possess one or more lactone rings, an exception being helminthogermacrene, see: Winter, R. E. K.; Dorn, F.; Arigoni, D. J. Org. Chem. 1980, 45, 4786.
-
(1980)
J. Org. Chem.
, vol.45
, pp. 4786
-
-
Winter, R.E.K.1
Dorn, F.2
Arigoni, D.3
-
24
-
-
0004138326
-
The sesquiterpenes
-
Newman, A. A., Ed.; Academic Press: London
-
(b) Roberts, J. S. The sesquiterpenes. In Chemistry of Terpenes and terpenoids; Newman, A. A., Ed.; Academic Press: London, 1972; pp 88-146.
-
(1972)
Chemistry of Terpenes and Terpenoids
, pp. 88-146
-
-
Roberts, J.S.1
-
28
-
-
46149129042
-
-
Valle, M. G.; Appendino, G.; Nano, G. M.; Picci, V. Phytochemistry 1987, 26, 253.
-
(1987)
Phytochemistry
, vol.26
, pp. 253
-
-
Valle, M.G.1
Appendino, G.2
Nano, G.M.3
Picci, V.4
-
29
-
-
0029586268
-
-
Gansser, D.; Pollak, F. C.; Berger, R. G. J. Nat. Prod. 1995, 58, 1790.
-
(1995)
J. Nat. Prod.
, vol.58
, pp. 1790
-
-
Gansser, D.1
Pollak, F.C.2
Berger, R.G.3
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30
-
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8244245641
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-
Only the interconversion of the conformations by rotation of the double bonds is considered
-
Only the interconversion of the conformations by rotation of the double bonds is considered.
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-
-
-
31
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0029042864
-
-
Piet, D. P.; Schrijvers, R.; Franssen, M. C. R.; de Groot, A. Tetrahedron 1995, 51, 6303.
-
(1995)
Tetrahedron
, vol.51
, pp. 6303
-
-
Piet, D.P.1
Schrijvers, R.2
Franssen, M.C.R.3
De Groot, A.4
-
32
-
-
0028274718
-
-
(a) Piet, D. P.; Franssen, M. C. R.; de Groot, A. Tetrahedron 1994, 50, 3169.
-
(1994)
Tetrahedron
, vol.50
, pp. 3169
-
-
Piet, D.P.1
Franssen, M.C.R.2
De Groot, A.3
-
33
-
-
0030593706
-
-
(b) Piet, D. P.; Franssen, M. C. R.; de Groot, A. Tetrahedron 1996, 52, 11273.
-
(1996)
Tetrahedron
, vol.52
, pp. 11273
-
-
Piet, D.P.1
Franssen, M.C.R.2
De Groot, A.3
-
34
-
-
0019462301
-
-
Huffman, J. W.; Hillenbrand, G. F. Tetrahedron 1981, 37, Supplement No.1, 269.
-
(1981)
Tetrahedron
, vol.37
, Issue.SUPPL. NO. 1
, pp. 269
-
-
Huffman, J.W.1
Hillenbrand, G.F.2
-
36
-
-
0028232283
-
-
For some recent examples in germacrane chemistry, see: (b) Minnaard, A. J.; Wijnberg, J. B. P. A.; de Groot, A. Tetrahedron 1994, 50, 4755, and (c) Zhabinskii, V. A.; Minnaard, A. J.; Wijnberg, J. B. P. A.; de Groot, A. J. Org. Chem. 1996, 61, 4022.
-
(1994)
Tetrahedron
, vol.50
, pp. 4755
-
-
Minnaard, A.J.1
Wijnberg, J.B.P.A.2
De Groot, A.3
-
37
-
-
0030010598
-
-
For some recent examples in germacrane chemistry, see: (b) Minnaard, A. J.; Wijnberg, J. B. P. A.; de Groot, A. Tetrahedron 1994, 50, 4755, and (c) Zhabinskii, V. A.; Minnaard, A. J.; Wijnberg, J. B. P. A.; de Groot, A. J. Org. Chem. 1996, 61, 4022.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 4022
-
-
Zhabinskii, V.A.1
Minnaard, A.J.2
Wijnberg, J.B.P.A.3
De Groot, A.4
-
38
-
-
0001220638
-
-
Agami, C.; Meynier, F.; Puchot, C.; Guilhem, J.; Pascard, C. Tetrahedron 1984, 40, 1031.
-
(1984)
Tetrahedron
, vol.40
, pp. 1031
-
-
Agami, C.1
Meynier, F.2
Puchot, C.3
Guilhem, J.4
Pascard, C.5
-
39
-
-
0027403311
-
-
Agami, C.; Kadouri-Puchot, C.; Le Guen, V. Tetrahedron: Asymmetry 1993, 4, 641.
-
(1993)
Tetrahedron: Asymmetry
, vol.4
, pp. 641
-
-
Agami, C.1
Kadouri-Puchot, C.2
Le Guen, V.3
-
40
-
-
0001569608
-
-
Li, Y.; Chen, X.; Shao, S.; Li, T. Ind. J. Chem. 1993, 32B, 356.
-
(1993)
Ind. J. Chem.
, vol.32 B
, pp. 356
-
-
Li, Y.1
Chen, X.2
Shao, S.3
Li, T.4
-
42
-
-
0001652973
-
-
Ireland, R. E.; Muchmore, D. C.; Hengartner, U. J. Am. Chem. Soc. 1972, 94, 5098.
-
(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 5098
-
-
Ireland, R.E.1
Muchmore, D.C.2
Hengartner, U.3
-
43
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8244246993
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note
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+, 9), 240 (33), 238 (100), 225 (7), 223 (21), 197 (20), 195 (60), 187 (34), 159 (36), 59 (48).
-
-
-
-
45
-
-
0011442739
-
-
Initially, it was thought that just the presence of the homoallylic double bond frustrated the mesylation of 11, see: Shoppee, C. W.; Summers, G. H. R. J. Chem. Soc. 1952, 3361.
-
(1952)
J. Chem. Soc.
, pp. 3361
-
-
Shoppee, C.W.1
Summers, G.H.R.2
-
46
-
-
0000846427
-
-
(a) Orrū, R. V. A.; Wijnberg, J. B. P. A.; Jenniskens, L. H. D.; de Groot, A. J. Org. Chem. 1993, 58, 1199.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 1199
-
-
Orru, R.V.A.1
Wijnberg, J.B.P.A.2
Jenniskens, L.H.D.3
De Groot, A.4
-
47
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-
0028316329
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-
(b) Orrū, R. V. A.; Wijnberg, J. B. P. A.; Bouwman, C. T.; de Groot, A. J. Org. Chem. 1994, 59, 374.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 374
-
-
Orru, R.V.A.1
Wijnberg, J.B.P.A.2
Bouwman, C.T.3
De Groot, A.4
-
48
-
-
8244240971
-
-
(c) Orr̄, R. V. A.; Wijnberg, J. B. P. A.; de Groot, A. J. Org. Chem. 1995, 60, 4233.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 4233
-
-
Orr, R.V.A.1
Wijnberg, J.B.P.A.2
De Groot, A.3
-
49
-
-
0012806632
-
-
Bastiaansen, P. M. F. M.; Wijnberg, J. B. P. A.; de Groot, A. J. Org. Chem. 1995, 60, 4240.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 4240
-
-
Bastiaansen, P.M.F.M.1
Wijnberg, J.B.P.A.2
De Groot, A.3
-
50
-
-
0004087865
-
-
Liebman, J. F., Greenberg, A., Eds.; VCH Publishers: New York, Chapter 3 and references cited therein
-
Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding and Delocalization; Liebman, J. F., Greenberg, A., Eds.; VCH Publishers: New York, 1988, Chapter 3 and references cited therein.
-
(1988)
Modern Models of Bonding and Delocalization
-
-
Paddon-Row, M.N.1
Jordan, K.D.2
-
53
-
-
84981783095
-
-
Steglich, W.; Höfle, G. Angew. Chem., Int. Ed. Engl. 1969, 8, 981.
-
(1969)
Angew. Chem., Int. Ed. Engl.
, vol.8
, pp. 981
-
-
Steglich, W.1
Höfle, G.2
-
54
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8244250014
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GC analysis revealed the presence of a small amount (< 10%) of another compound, probably a double bond isomer of 10
-
GC analysis revealed the presence of a small amount (< 10%) of another compound, probably a double bond isomer of 10.
-
-
-
-
55
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8244240256
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Reference 8, van Beek et al.
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Beek, V.1
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