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(a) Putkonen, T.; Tolvanen, A.; Jokela, R. Tetrahedron Lett. 2001, 42, 6593-6594.
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0348041988
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Luo, S.; Zificsak, C. A.; Hsung, R. P. Org. Lett. 2003, 5, 4709 4712.
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Wilkinson, J.A.1
Ardes-Guisot, N.2
Ducki, S.3
Leonard, J.4
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9
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66149115711
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Using the classical biogenetic numbering proposed by Le Men and Taylor which has the advantage of showing the structural homogeneity within the apparent diversity of these alkaloids
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Using the classical "biogenetic" numbering proposed by Le Men and Taylor which has the advantage of showing the structural homogeneity within the apparent diversity of these alkaloids.
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10
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66149134152
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With the exception of nitraraine which structure is questioned. An extensive survey on Nitraria alkaloids will soon be disclosed elsewhere as a review article
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With the exception of nitraraine which structure is questioned. An extensive survey on Nitraria alkaloids will soon be disclosed elsewhere as a review article.
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11
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20544462630
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(a) Gravel, E.; Poupon, E.; Hocquemiller, R. Org. Lett. 2005, 7, 2497-2499.
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Gravel, E.1
Poupon, E.2
Hocquemiller, R.3
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(b) Gravel, E.; Poupon, E.; Hocquemiller, R. Tetrahedron 2006, 62, 5248-5253.
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Tetrahedron
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Gravel, E.1
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13
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85013539502
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Elsevier: Amsterdam, and references therein
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(a) Wanner, M. J.; Koomen, G.-J. In Studies in Natural Products Chemistry: Stereoselectivity in Synthesis and Biosynthesis of Lupine and Nitraria Alkaloids; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1994; Vol. 14, pp 731-768, and references therein.
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Studies in Natural Products Chemistry: Stereoselectivity in Synthesis and Biosynthesis of Lupine and Nitraria Alkaloids; Atta-ur-Rahman, Ed
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Wanner, M.J.1
Koomen, G.-J.2
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16
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0000735954
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François, D.; Lallemand, M.-C̃ Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. J. Org. Chem. 1997, 62, 8914-8916.
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François, D.1
Lallemand, M.-C.2
Selkti, M.3
Tomas, A.4
Kunesch, N.5
Husson, H.-P.6
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17
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0031929582
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(e) François, D.; Lallemand, M. C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Angew. Chem., Int. Ed. 1998, 37, 104-105.
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Angew. Chem., Int. Ed
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François, D.1
Lallemand, M.C.2
Selkti, M.3
Tomas, A.4
Kunesch, N.5
Husson, H.-P.6
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18
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66149087801
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This is of particular interest in terms of chemotaxonomy. The two families are not related to one another
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This is of particular interest in terms of chemotaxonomy. The two families are not related to one another.
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19
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34848883609
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Pham, V. C.; Jossang, A.; Sévenet, T.; Nguyen, V. H.; Bodo, B. Tetrahedron 2007, 63, 11244-11249.
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(2007)
Tetrahedron
, vol.63
, pp. 11244-11249
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Pham, V.C.1
Jossang, A.2
Sévenet, T.3
Nguyen, V.H.4
Bodo, B.5
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20
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36849010701
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Pham, V. C.; Jossang, A.; Sévenet, T.; Nguyen, V. H.; Bodo, B. J. Org. Chem. 2007, 72, 9826-9829.
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(2007)
J. Org. Chem
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, pp. 9826-9829
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Pham, V.C.1
Jossang, A.2
Sévenet, T.3
Nguyen, V.H.4
Bodo, B.5
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21
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33751500609
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Compound 10 was reported before, it was characterized, at this time, as its perfluorobenzylhydroxylamine adduct. See: Tashima, T.; Imai, M.; Kuroda, Y.; Yagi, S.; Nakagawa, T. J. Org. Chem. 1991, 56, 694-697. No yield of the reaction was provided.
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Compound 10 was reported before, it was characterized, at this time, as its perfluorobenzylhydroxylamine adduct. See: Tashima, T.; Imai, M.; Kuroda, Y.; Yagi, S.; Nakagawa, T. J. Org. Chem. 1991, 56, 694-697. No yield of the reaction was provided.
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22
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66149151490
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The yield is obviously low and could easily constitute a major drawback of the synthesis, but experimentally speaking, glutaraldehyde 5 is a cheap reagent and 10 is the most apolar compound of the reaction based on silica gel TLC profile which renders its purification by chomatog- raphy easy. In practise, 15 g of 5 give 3-4gof 10 in a reproducible manner. We will give a full account of the other compounds isolated in due course, but 5, as suspected, mainly gives complex polymers.
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The yield is obviously low and could easily constitute a major drawback of the synthesis, but experimentally speaking, glutaraldehyde 5 is a cheap reagent and 10 is the most apolar compound of the reaction based on silica gel TLC profile which renders its purification by chomatog- raphy easy. In practise, 15 g of 5 give 3-4gof 10 in a reproducible manner. We will give a full account of the other compounds isolated in due course, but 5, as suspected, mainly gives complex polymers.
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23
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66149098280
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This intermediate is putative and the pathway depicted is one among others. The treatment of 10 in the same conditions but without tryptamine did not allow the isolation of 7 10 remained mostly unchanged and was partly converted into O-acetyl-10
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This intermediate is putative and the pathway depicted is one among others. The treatment of 10 in the same conditions but without tryptamine did not allow the isolation of 7 (10 remained mostly unchanged and was partly converted into O-acetyl-10).
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24
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66149105224
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Which could be isolated as a single diastereomer by recrystallization of a trifluoroacetate salt precipitated from H2.O/CH3CN 8:2
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3CN (8:2).
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25
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66149148404
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See Supporting Information. Data were in agreement with the extensive analysis reported in R. P. Hsung's work (ref 4).
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See Supporting Information. Data were in agreement with the extensive analysis reported in R. P. Hsung's work (ref 4).
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26
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66149155924
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Analytical conditions, see Supporting Information, could not be transposed to preparative HPLC due to solubility/precipitation issues
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Analytical conditions, see Supporting Information, could not be transposed to preparative HPLC due to solubility/precipitation issues.
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27
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66149112226
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As exemplified, here, by the fact that 1 is isolated as an optically inactive compound as it is the case for a large majority of Nitraria alkaloids with the exception of simple spiro-alkaloids such as nitramine. For a recent discussion on the impact of spontaneity in the biosynthesis of natural products, see: Poupon, E.; Gravel, E. Eur. J. Org. Chem. 2008, 27-42.
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As exemplified, here, by the fact that 1 is isolated as an optically inactive compound as it is the case for a large majority of Nitraria alkaloids with the exception of simple spiro-alkaloids such as nitramine. For a recent discussion on the impact of spontaneity in the biosynthesis of natural products, see: Poupon, E.; Gravel, E. Eur. J. Org. Chem. 2008, 27-42.
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28
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0007964365
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Tulyaganov, T. S.; Ibragimov, A. A.; Yunusov, S. Y.; Yu, Chem. Nat. Compd. 1982, 18, 604-606.
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(1982)
Chem. Nat. Compd
, vol.18
, pp. 604-606
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Tulyaganov, T.S.1
Ibragimov, A.A.2
Yunusov, S.Y.3
Yu4
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30
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34250112029
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Tulyaganov, T. S.; Ibragimov, A. A.; Yunusov, S.; Yu, Chem. Nat. Compd. 1983, 20, 378-379.
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(1983)
Chem. Nat. Compd
, vol.20
, pp. 378-379
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Tulyaganov, T.S.1
Ibragimov, A.A.2
Yunusov, S.3
Yu4
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