-
1
-
-
79953900109
-
-
Examples of terpenoids containing in their structure a cyclopentane core with contiguous asymmetric centers
-
Examples of terpenoids containing in their structure a cyclopentane core with contiguous asymmetric centers: Rossinone, B; Appleton, D. R.; Chuen, C. S.; Berridge, M. V.; Webb, V. L.; Copp, B. R. J. Org. Chem. 2006, 74, 9195-9198
-
(2006)
J. Org. Chem.
, vol.74
, pp. 9195-9198
-
-
Rossinone, B.1
Appleton, D.R.2
Chuen, C.S.3
Berridge, M.V.4
Webb, V.L.5
Copp, B.R.6
-
2
-
-
33749150578
-
-
Guaianes
-
Guaianes: Blay, G.; García, B.; Molina, E.; Pedro, J. R. J. Org. Chem. 2006, 71, 7866-7869
-
(2006)
J. Org. Chem.
, vol.71
, pp. 7866-7869
-
-
Blay, G.1
García, B.2
Molina, E.3
Pedro, J.R.4
-
3
-
-
64549101152
-
-
Dobellanes
-
Dobellanes: Wang, Y.; Harrison, L. J.; Tan, B. C. Tetrahedron 2009, 65, 4035-4043
-
(2009)
Tetrahedron
, vol.65
, pp. 4035-4043
-
-
Wang, Y.1
Harrison, L.J.2
Tan, B.C.3
-
4
-
-
70349443542
-
-
Hydroxylcyclopentylbotryococcene
-
Hydroxylcyclopentylbotryococcene: Pan, J.-J.; Bugni, T. S.; Poulter, C. D. J. Org. Chem. 2009, 74, 7562-7565
-
(2009)
J. Org. Chem.
, vol.74
, pp. 7562-7565
-
-
Pan, J.-J.1
Bugni, T.S.2
Poulter, C.D.3
-
5
-
-
15444375348
-
-
Iridanes
-
Iridanes: Barrero, A. F.; Arseniyadis, S.; Herrador, M. M.; Quilez del Moral, J. F.; Arteaga, J. F.; Sánchez, E. M. Synlett 2005, 591-594
-
(2005)
Synlett
, pp. 591-594
-
-
Barrero, A.F.1
Arseniyadis, S.2
Herrador, M.M.3
Quilez Del Moral, J.F.4
Arteaga, J.F.5
Sánchez, E.M.6
-
6
-
-
33748649494
-
-
Fusicoccanes
-
Fusicoccanes: Kato, N. S.; Zhang, C.-S.; Matsui, T.; Iwabuchi, H.; Mori, A.; Ballio, A.; Sassa, T. J. Chem. Soc., Perkin Trans. 1: Org, Biomol. Chem. 1998, 16, 2473-2474
-
(1998)
J. Chem. Soc., Perkin Trans. 1: Org, Biomol. Chem.
, vol.16
, pp. 2473-2474
-
-
Kato, N.S.1
Zhang, C.-S.2
Matsui, T.3
Iwabuchi, H.4
Mori, A.5
Ballio, A.6
Sassa, T.7
-
7
-
-
73049085067
-
-
For a recent review:;;;;, For asymmetric synthesis of chokols, see:;; Synlett 2006, 2223-2226
-
For a recent review: Barrero, A. F.; Quílez del Moral, J. F.; Herrador, M. M.; Rodríguez, H.; Pérez Morales, C. Curr. Org. Chem. 2009, 13, 1164-1181 For asymmetric synthesis of chokols, see: Groth, U.; Kesenheimer, C; Kreye, P. Synlett 2006, 2223-2226
-
(2009)
Curr. Org. Chem.
, vol.13
, pp. 1164-1181
-
-
Barrero, A.F.1
Quílez Del Moral, J.F.2
Herrador, M.M.3
Rodríguez, H.4
Pérez Morales, C.5
Groth, U.6
Kesenheimer, C.7
Kreye, P.8
-
9
-
-
0028864553
-
-
Urban, E.; Knuehl, G.; Helmchen, G. Tetrahedron 1995, 51, 13031-13038
-
(1995)
Tetrahedron
, vol.51
, pp. 13031-13038
-
-
Urban, E.1
Knuehl, G.2
Helmchen, G.3
-
10
-
-
55449103171
-
-
For recent papers involving synthesis of cyclopentanes, see
-
For recent papers involving synthesis of cyclopentanes, see: Zhao, G.-L.; Ibrahem, I.; Dziedzic, P.; Sun, J.; Bonneau, C.; Cordova, A. Chem. - Eur. J. 2008, 14, 10007-10011
-
(2008)
Chem. - Eur. J.
, vol.14
, pp. 10007-10011
-
-
Zhao, G.-L.1
Ibrahem, I.2
Dziedzic, P.3
Sun, J.4
Bonneau, C.5
Cordova, A.6
-
11
-
-
51549098991
-
-
Dake, G. R.; Fenster, E. E.; Patrick, B. O. J. Org. Chem. 2008, 73, 6711-6715
-
(2008)
J. Org. Chem.
, vol.73
, pp. 6711-6715
-
-
Dake, G.R.1
Fenster, E.E.2
Patrick, B.O.3
-
14
-
-
70349881451
-
-
Qu, J.-P.; Deng, C.; Zhou, J.; Sun, X.-L.; Tang, Y. J. Org. Chem. 2009, 74, 7684-7689
-
(2009)
J. Org. Chem.
, vol.74
, pp. 7684-7689
-
-
Qu, J.-P.1
Deng, C.2
Zhou, J.3
Sun, X.-L.4
Tang, Y.5
-
15
-
-
77950258096
-
-
Beckett, J. S.; Beckett, J. D.; Hofferberth, J. E.. Org. Lett. 2010, 12, 1408-1411
-
(2010)
Org. Lett.
, vol.12
, pp. 1408-1411
-
-
Beckett, J.S.1
Beckett, J.D.2
Hofferberth, J.E.3
-
16
-
-
75649095991
-
-
Kiss, L.; Forró, E.; Sillanpää, R.; Fülöp, F. Synthesis 2010, 153-160
-
(2010)
Synthesis
, pp. 153-160
-
-
Kiss, L.1
Forró, E.2
Sillanpää, R.3
Fülöp, F.4
-
17
-
-
77953558234
-
-
Davies, J. J.; Krulle, T. M.; Burton, J. W. Org. Lett. 2010, 12, 2738-2741
-
(2010)
Org. Lett.
, vol.12
, pp. 2738-2741
-
-
Davies, J.J.1
Krulle, T.M.2
Burton, J.W.3
-
18
-
-
85004704421
-
-
The preparation of racemic 1 has been previously reported as a mixture of diastereomers in eight steps
-
The preparation of racemic 1 has been previously reported as a mixture of diastereomers in eight steps: Tanimori, S.; Ueda, T.; Nakayama, M. Biosci. Biotechnol. Biochem. 1993, 57, 1713-1715
-
(1993)
Biosci. Biotechnol. Biochem.
, vol.57
, pp. 1713-1715
-
-
Tanimori, S.1
Ueda, T.2
Nakayama, M.3
-
19
-
-
33745353059
-
-
Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron 2006, 62, 7505-7511
-
(2006)
Tetrahedron
, vol.62
, pp. 7505-7511
-
-
Wender, P.A.1
Croatt, M.P.2
Witulski, B.3
-
20
-
-
33845280764
-
-
For pioneering work in this field, see
-
For pioneering work in this field, see: Nugent, W. A.; RajanBabu, T. V. J. Am. Chem. Soc. 1988, 110, 8561-8562
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 8561-8562
-
-
Nugent, W.A.1
Rajanbabu, T.V.2
-
22
-
-
0000533091
-
-
RajanBabu, T. V.; Nugent, W. A.; Beattie, M. S. J. Am. Chem. Soc. 1990, 112, 6408-6409
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 6408-6409
-
-
Rajanbabu, T.V.1
Nugent, W.A.2
Beattie, M.S.3
-
23
-
-
0040155755
-
-
For reviews, see:; Chem. Rev. 2000, 100, 2771-2788
-
RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986-997 For reviews, see: Gansäuer, A.; Bluhm, H. Chem. Rev. 2000, 100, 2771-2788
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 986-997
-
-
Rajanbabu, T.V.1
Nugent, W.A.2
Gansäuer, A.3
Bluhm, H.4
-
24
-
-
0005208178
-
-
In;;, Eds.; Wiley-VCH: Weinheim, Germany,; Vol., pp - 220
-
Gansäuer, A.; Pierobon, M. In Radicals in Organic Synthesis; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 207 - 220.
-
(2001)
Radicals in Organic Synthesis
, vol.2
, pp. 207
-
-
Gansäuer, A.1
Pierobon, M.2
Renaud, P.3
Sibi, M.P.4
-
27
-
-
3543021271
-
-
In;, Ed.; Wiley-VCH: Weinheim, Germany,; pp - 450
-
Gansäuer, A.; Rinker, B. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 435 - 450.
-
(2002)
Titanium and Zirconium in Organic Synthesis
, pp. 435
-
-
Gansäuer, A.1
Rinker, B.2
Marek, I.3
-
28
-
-
0344667717
-
-
Gansäuer, A.; Lauterbach, T.; Narayan, S. Angew. Chem., Int. Ed. 2003, 42, 5556-5573
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 5556-5573
-
-
Gansäuer, A.1
Lauterbach, T.2
Narayan, S.3
-
29
-
-
33746115656
-
-
Cuerva, J. M.; Justicia, J.; Oller-Lopez, J. L.; Bazdi, B.; Oltra, J. E. Mini-Rev. Org. Chem. 2006, 3, 23-35
-
(2006)
Mini-Rev. Org. Chem.
, vol.3
, pp. 23-35
-
-
Cuerva, J.M.1
Justicia, J.2
Oller-Lopez, J.L.3
Bazdi, B.4
Oltra, J.E.5
-
30
-
-
33746073438
-
-
Cuerva, J. M.; Justicia, J.; Oller-Lopez, J. L.; Oltra, J. E. Top. Curr. Chem. 2006, 264, 63-91
-
(2006)
Top. Curr. Chem.
, vol.264
, pp. 63-91
-
-
Cuerva, J.M.1
Justicia, J.2
Oller-Lopez, J.L.3
Oltra, J.E.4
-
31
-
-
33645533829
-
-
For references of the catalytic version, see:; Chem. Commun. 1998, 2143-2144
-
Barrero, A. F.; Quilez del Moral, J. F.; Sanchez, E. M.; Arteaga, J. F. Eur. J. Org. Chem. 2006, 1627-1641 For references of the catalytic version, see: Gansäuer, A.; Bluhm, H. Chem. Commun. 1998, 2143-2144
-
(2006)
Eur. J. Org. Chem.
, pp. 1627-1641
-
-
Barrero, A.F.1
Quilez Del Moral, J.F.2
Sanchez, E.M.3
Arteaga, J.F.4
Gansäuer, A.5
Bluhm, H.6
-
32
-
-
0031882645
-
-
Gansäuer, A.; Pierobon, M.; Bluhm, H. Angew. Chem., Int. Ed. 1998, 37, 101-103
-
(1998)
Angew. Chem., Int. Ed.
, vol.37
, pp. 101-103
-
-
Gansäuer, A.1
Pierobon, M.2
Bluhm, H.3
-
33
-
-
0032539234
-
-
Gansäuer, A.; Bluhm, H.; Pierobon, M. J. Am. Chem. Soc. 1998, 120, 12849-12859
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 12849-12859
-
-
Gansäuer, A.1
Bluhm, H.2
Pierobon, M.3
-
34
-
-
0041350396
-
-
Barrero, A. F.; Rosales, A.; Cuerva, J. M.; Oltra, J. E. Org. Lett. 2003, 5, 1935-1938
-
(2003)
Org. Lett.
, vol.5
, pp. 1935-1938
-
-
Barrero, A.F.1
Rosales, A.2
Cuerva, J.M.3
Oltra, J.E.4
-
36
-
-
15944408848
-
-
Enemãrke, R. J.; Larsem, J.; Hjøluund, G. H.; Skrydstrup, T.; Daasbjerg, K. Organometallics 2005, 24, 1252-1262
-
(2005)
Organometallics
, vol.24
, pp. 1252-1262
-
-
Enemãrke, R.J.1
Larsem, J.2
Hjøluund, G.H.3
Skrydstrup, T.4
Daasbjerg, K.5
-
37
-
-
79953885994
-
-
Diastereoselective epoxide openings were already described by Nugent and RajanBabu, including cases with functionalized carbohydrate-derived epoxyalkenes; see ref 6d
-
Diastereoselective epoxide openings were already described by Nugent and RajanBabu, including cases with functionalized carbohydrate-derived epoxyalkenes; see ref 6d.
-
-
-
-
39
-
-
27344452533
-
-
Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Phys. 2005, 123, 161103-1611103-4
-
(2005)
J. Chem. Phys.
, vol.123
, pp. 161103-16111034
-
-
Zhao, Y.1
Schultz, N.E.2
Truhlar, D.G.3
-
40
-
-
26344435738
-
-
Schafer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577
-
(1992)
J. Chem. Phys.
, vol.97
, pp. 2571-2577
-
-
Schafer, A.1
Horn, H.2
Ahlrichs, R.3
-
41
-
-
79953868083
-
-
note
-
Acyclic radicals Ia-d should be considered as conformers since according to the theoretical data the geometry of the carbon where the radical is located is trigonal (note that the x, y, and z Cartesian coordinates for all theoretically calculated species are provided in Supporting Information). On the other hand, the cyclic radicals IIa-d resulting from the cyclization (two stereocenters are created) are diastereomers.
-
-
-
-
43
-
-
0042468148
-
-
2TiCl radical, has been reported in related systems where no template effect can be involved
-
2TiCl radical, has been reported in related systems where no template effect can be involved: Gansäuer, A.; Rinker, B.; Pierobon, M.; Grimme, S.; Gerenkamp, M.; Mück-Lichtenfeld, C. Angew. Chem., Int. Ed. 2003, 42, 3687-3690
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 3687-3690
-
-
Gansäuer, A.1
Rinker, B.2
Pierobon, M.3
Grimme, S.4
Gerenkamp, M.5
Mück-Lichtenfeld, C.6
-
44
-
-
79953900629
-
-
note
-
When 3a and 3b were subjected separately to the reaction conditions, the same mixture of products were obtained. Consequently, a balance between the axially and equatorially disposed radicals initially generated in each case should occur via a planar structure where the electron would be located in a p orbital. The theoretically calculated planar or quasi-planar disposition of the corresponding carbon in the acyclic radicals Ia-d supports this hypothesis.
-
-
-
-
45
-
-
85007976342
-
-
Chemical conversions of chokol G to chokol K and chokol B, the latter as a mixture of diastereoisomers, has been previously reported
-
Chemical conversions of chokol G to chokol K and chokol B, the latter as a mixture of diastereoisomers, has been previously reported: Tanimori, S.; Ueda, T.; Nakayama, M. Biosci. Biotechnol. Biochem. 1994, 58, 1174-1176
-
(1994)
Biosci. Biotechnol. Biochem.
, vol.58
, pp. 1174-1176
-
-
Tanimori, S.1
Ueda, T.2
Nakayama, M.3
-
46
-
-
67650984682
-
-
For a review on this subject, see
-
For a review on this subject, see: Young, I. S.; Baran, P. S. Nature 2009, 1, 193-205
-
(2009)
Nature
, vol.1
, pp. 193-205
-
-
Young, I.S.1
Baran, P.S.2
-
47
-
-
33748677051
-
-
For previous synthetic reports on this type of compounds, see ref 1. The last synthesis of chokols reported was the Groth asymmetric preparation of chokol A:;;,. The overall yield of this convergent approach was 27% over 6 steps, starting from a chiral ester and a high order cuprate, which in turn were prepared in 3 and 5 steps, respectively
-
For previous synthetic reports on this type of compounds, see ref 1. The last synthesis of chokols reported was the Groth asymmetric preparation of chokol A: Groth, U.; Kesenheimer, C; Kreye, P. Synlett 2006, 2223-2226. The overall yield of this convergent approach was 27% over 6 steps, starting from a chiral ester and a high order cuprate, which in turn were prepared in 3 and 5 steps, respectively
-
(2006)
Synlett
, pp. 2223-2226
-
-
Groth, U.1
Kesenheimer, C.2
Kreye, P.3
-
48
-
-
79953840061
-
-
(+)-Nerolidol can be obtained directly in multigram quantities from Inula viscosa. For details see the Experimental Section
-
(+)-Nerolidol can be obtained directly in multigram quantities from Inula viscosa. For details see the Experimental Section.
-
-
-
-
49
-
-
0004318687
-
-
Koshino, H.; Togiya, S.; Terada, S.; Yoshihara, T.; Sakamura, S.; Shimanuki, T.; Sato, T.; Tajimi, A. Agric. Biol. Chem. 1989, 53, 789-796
-
(1989)
Agric. Biol. Chem.
, vol.53
, pp. 789-796
-
-
Koshino, H.1
Togiya, S.2
Terada, S.3
Yoshihara, T.4
Sakamura, S.5
Shimanuki, T.6
Sato, T.7
Tajimi, A.8
-
50
-
-
0141712450
-
-
Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M. J. Org. Chem. 1992, 10, 2768-2771
-
(1992)
J. Org. Chem.
, vol.10
, pp. 2768-2771
-
-
Sharpless, K.B.1
Amberg, W.2
Bennani, Y.L.3
Crispino, G.A.4
Hartung, J.5
Jeong, K.S.6
Kwong, H.L.7
Morikawa, K.8
Wang, Z.M.9
-
51
-
-
70449723521
-
-
Justicia, J.; Jiménez, T.; Morcillo, S. P.; Cuerva, J. M.; Oltra, J. E. Tetrahedron 2009, 65, 10837-10841
-
(2009)
Tetrahedron
, vol.65
, pp. 10837-10841
-
-
Justicia, J.1
Jiménez, T.2
Morcillo, S.P.3
Cuerva, J.M.4
Oltra, J.E.5
-
52
-
-
0025634548
-
-
The optical rotatory power of our (+)-natural compound (+12.2°) is comparable to that of (-)-nerolidol (-12.5°) obtained synthetically from (-)-linalool:;;;;,. These values suggest a high optical richness for our (+)-nerolidol
-
The optical rotatory power of our (+)-natural compound (+12.2°) is comparable to that of (-)-nerolidol (-12.5°) obtained synthetically from (-)-linalool: David, E.; Cane, D. E.; Ha, H.-J.; McIlwaine, D: B.; Pascoe, K. O. Tetrahedron Lett. 1990, 31, 7553-7554. These values suggest a high optical richness for our (+)-nerolidol
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 7553-7554
-
-
David, E.1
Cane, D.E.2
Ha, H.-J.3
McIlwaine, D.B.4
Pascoe, K.O.5
|