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79956152585
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2) as an efficient nitrogen nucleophile for synthesis of medium- or large-sized cyclic amines
-
2) as an efficient nitrogen nucleophile for synthesis of medium- or large-sized cyclic amines.
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32
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33845553050
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34
-
-
79956101450
-
-
note
-
2 was finally chosen not only because it can give the best yield but also because it can be readily deprotected into the free amine 1, leaving the other functionalities of the substrate untouched.
-
-
-
-
35
-
-
79956100933
-
-
Similar conditions used by the Heathcock group in their fawcettimine total synthesis. See ref 5b
-
Similar conditions used by the Heathcock group in their fawcettimine total synthesis. See ref 5b.
-
-
-
-
36
-
-
79956098839
-
-
The ratio of undesired α isomer to desired β is high, up to 2:1
-
The ratio of undesired α isomer to desired β is high, up to 2:1.
-
-
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37
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0030665236
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38
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12344303950
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39
-
-
85008007688
-
-
D -15.6 (c 1.0, EtOH)
-
D -15.6 (c 1.0, EtOH). Ishii, H.; Yasui, B.; Nishino, R.; Harayama, T.; Inubushi, Y. Chem. Pharm. Bull. 1970, 18, 1880-1888
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-
40
-
-
79956090066
-
-
3 failed to give the products
-
3 failed to give the products.
-
-
-
-
41
-
-
0041807380
-
-
Griffith, W. P.; Ley, S. V.; Whitcombe, G. P.; White, A. D. J. Chem. Soc., Chem. Commun. 1987, 1625-1627
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42
-
-
70349922853
-
-
2 in total synthesis
-
2 in total synthesis, see Nicolaou, K. C.; Ellery, S. P.; Chen, J. S. Angew. Chem., Int. Ed. 2009, 48, 7140-7165
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Nicolaou, K.C.1
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-
43
-
-
79956150481
-
-
D +89 (c 0.55, MeOH)
-
D +89 (c 0.55, MeOH).
-
-
-
-
44
-
-
77958035710
-
-
During the early stage of preparation of this manuscript, one elegant synthesis of lycoflexine has been published by Mulzer et al.: Ramharter, J.; Weinstabl, H.; Mulzer, J. J. Am. Chem. Soc. 2010, 132, 14338-14339. Mulzer used similar conditions as Ayer did, namely, acidic aqueous HCHO in extended reaction time (48 h) employed to accomplish this important biomimetic transformation. The first asymmetric total synthesis of lycoflexine including the assignment of the absolute configuration was reported by the Mulzer group.
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Ramharter, J.1
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Mulzer, J.3
-
45
-
-
0015527097
-
-
A similar protocol adopted by the Evans group in their total synthesis of the Lycopodium alkaloid luciduline; see
-
A similar protocol adopted by the Evans group in their total synthesis of the Lycopodium alkaloid luciduline; see Scott, W. L.; Evans, D. A. J. Am. Chem. Soc. 1972, 94, 4779-4780
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Scott, W.L.1
Evans, D.A.2
-
46
-
-
79956097514
-
-
note
-
D +5.0 (c 0.42, DCM).
-
-
-
|