-
1
-
-
84988122577
-
-
For the synthesis of (-)-β-santalol (very strong sandalwood odor) and (+)-β-santalol (odorless) through the use of chiral auxiliaries see
-
a) For the synthesis of (-)-β-santalol (very strong sandalwood odor) and (+)-β-santalol (odorless) through the use of chiral auxiliaries see: A. Krotz, G. Helmchen, Liebigs Ann. Chem. 1994, 601;
-
(1994)
Liebigs Ann. Chem
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Krotz, A.1
Helmchen, G.2
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3
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84987584120
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for related studies, see
-
for related studies, see : W Oppolzer, C. Chapuis, D. Dupuis, M. Guo, HeIv. Chim. Acta 1985, 68, 2100;
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(1985)
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Oppolzer, W.1
Chapuis, C.2
Dupuis, D.3
Guo, M.4
-
5
-
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0001545486
-
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for the synthesis of (±)-β-santalol, see
-
b) for the synthesis of (±)-β-santalol, see: D. Solas, J. Wolinsky, J. Org. Chem. 1983, 48, 1988;
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(1983)
J. Org. Chem
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70349959599
-
-
The wood of Santalum album L. has been overharvested, and the Indian government now bans exportation of this threatened species (2004 IUCN Red List).
-
The wood of Santalum album L. has been overharvested, and the Indian government now bans exportation of this threatened species (2004 IUCN Red List).
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11
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46749159211
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X. Moreau, J.-P. Goddard, M. Bernard, G. Lemière, J. M. LópezRomero, E. Mainetti, N Marion, V Mouriès, S. Thorimbert, L. Fensterbank, M. Malacria, Adv. Synth. Catal. 2008, 350, 43;
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48
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c) see also: C. M. Grisé, E. M. Rodrigue, L. Barriault, Tetrahedron 2008, 64, 797.
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0345058933
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N Bluthe, J. Goré, M. Malacria, Tetrahedron 1986, 42,1333.
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Bluthe, N.1
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56
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-
70349964243
-
-
The copper reagent possibly produces an intermediate of type B with more-localized charges and thus favors the fragmentation pathway. As B and C are two extreme representations of the same intermediate, the ease of fragmentation may also be related to the unlikelihood that a 1,2-R shift would take place in this system (owing to the electrophilicity of the carbenoid).
-
The copper reagent possibly produces an intermediate of type B with more-localized charges and thus favors the fragmentation pathway. As B and C are two extreme representations of the same intermediate, the ease of fragmentation may also be related to the unlikelihood that a 1,2-R shift would take place in this system (owing to the electrophilicity of the carbenoid).
-
-
-
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58
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0034600250
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K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243;
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70349939330
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c) Y. Hayashi, S. Samanta, H. Gotoh, H. Ishikawa, Angew. Chem. 2008, 120,6136;
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Chu, Q.1
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63
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34547224498
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(enantiomer)
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M. Lemay, L. Aumand, W. W. Ogilvie, Adv. Synth. Catal. 2007, 349, 441 (enantiomer);
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Lemay, M.1
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64
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35548980803
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26944476677
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C. S. Pecinovsky, G. D. Nicodemus, D. L. Gin, Chem. Mater. 2005, 17, 4889.
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66
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70349959583
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-
2O) according to
-
2O) according to:
-
-
-
-
67
-
-
0000826366
-
-
D. Seebach, R. Dahinden, R. E. Marti, A. K. Beck, D. A. Plattner, F. N. M. Kühnle, J. Org. Chem. 1995, 60, 1788.
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(1995)
J. Org. Chem
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-
Seebach, D.1
Dahinden, R.2
Marti, R.E.3
Beck, A.K.4
Plattner, D.A.5
Kühnle, F.N.M.6
-
68
-
-
70349950412
-
-
We chose to prepare compounds 8 and 9 by this method based on a known procedure
-
We chose to prepare compounds 8 and 9 by this method based on a known procedure
-
-
-
-
69
-
-
70349937757
-
-
G Joachimsmann-Dufresne, as the conditions are neutral (in contrast to acetate pyrolysis), industrially sound (as opposed to mesylate elimination), and high-yielding.
-
(G Joachimsmann-Dufresne, M. Blanchard, Bull. Soc. Chim. Fr. 1968, 385) , as the conditions are neutral (in contrast to acetate pyrolysis), industrially sound (as opposed to mesylate elimination), and high-yielding.
-
(1968)
Bull. Soc. Chim. Fr
, vol.385
-
-
Joachimsmann-Dufresne, G.1
Blanchard, M.2
-
70
-
-
70349957850
-
-
Surprisingly, the ee values of 8 and, to a larger extent, 9 were lower than those of 6 and 7, although the diastereomeric ratio remained the same. Compounds 8 and 9 possibly undergo a thermal 1,2-H shift.
-
Surprisingly, the ee values of 8 and, to a larger extent, 9 were lower than those of 6 and 7, although the diastereomeric ratio remained the same. Compounds 8 and 9 possibly undergo a thermal 1,2-H shift.
-
-
-
-
71
-
-
0000161573
-
-
K. J. H. Kruithof, R. F. Schmitz, G. W. Klumpp, Tetrahedron 1983, 39, 3073.
-
(1983)
Tetrahedron
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Kruithof, K.J.H.1
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72
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48749136767
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-
For another example, see
-
For another example, see: R. L. Snowden, R. Näf, Tetrahedron Lett. 1984, 25, 2877.
-
(1984)
Tetrahedron Lett
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-
-
Snowden, R.L.1
Näf, R.2
-
73
-
-
70349941012
-
-
For a long synthesis of (±)-3 of unspecified configuration (8 steps, 13% yield), see
-
For a long synthesis of (±)-3 of unspecified configuration (8 steps, 13% yield), see:
-
-
-
-
74
-
-
70349954618
-
-
spectral data are not reported.
-
M. Baumann, W Hoffmann (BASF), EP 0010213, 1980 [Chem. Abstr. 1980, 93, 185844]; spectral data are not reported.
-
(1980)
EP 0010213, 1980 Chem. Abstr
, vol.93
, pp. 185844
-
-
Baumann, M.1
Hoffmann, W.2
-
75
-
-
70349948698
-
-
4 in toluene (70°C, 1 h) led to completely selective cyclization-fragmentation; however, the yield was inferior (55%).
-
4 in toluene (70°C, 1 h) led to completely selective cyclization-fragmentation; however, the yield was inferior (55%).
-
-
-
-
77
-
-
70349957849
-
-
We are presently tackling the longstanding problem that no more general alternative exists for the synthesis of Z trisubstituted allylic alcohols.
-
We are presently tackling the longstanding problem that no more general alternative exists for the synthesis of Z trisubstituted allylic alcohols.
-
-
-
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