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20
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84863244401
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note
-
Oxidation state manipulation and/or functionalization would most likely be required for such a fragmentation. Indoline 28, a reported degradation derivative of aspidodasycarpine (see ref 9), possesses the carbon scaffold contained in the akuammiline alkaloids. All members of this class can be considered as oxidized and functionalized analogues of this scaffold. (Chemical Equation Presented)
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21
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0029057576
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Lactone (-)-15 was prepared via the reported four-step enzyme-mediated asymmetrization and functionalization of mesocyclohex-4-ene-1,2-dimethanol. See: (a)
-
Lactone (-)-15 was prepared via the reported four-step enzyme-mediated asymmetrization and functionalization of mesocyclohex-4-ene-1,2-dimethanol. See: (a) Danieli, B.; Lesma, G.; Mauro, M.; Palmisano, G.; Passarella, D. J. Org. Chem. 1995, 60, 2506-2513.
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J. Org. Chem.
, vol.60
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Danieli, B.1
Lesma, G.2
Mauro, M.3
Palmisano, G.4
Passarella, D.5
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22
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0028088052
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(b) Danieli, B.; Lesma, G.; Mauro, M.; Palmisano, G.; Passarella, D. Tetrahedron 1994, 50, 8837-8852.
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(1994)
Tetrahedron
, vol.50
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Danieli, B.1
Lesma, G.2
Mauro, M.3
Palmisano, G.4
Passarella, D.5
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23
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0025684628
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See the Supporting Information for a modified preparation amenable to scale-up
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(c) Danieli, B.; Lesma, G.; Mauro, M.; Palmisano, G.; Passarella, D. Tetrahedron: Asymmetry 1990, 1, 793-800. See the Supporting Information for a modified preparation amenable to scale-up.
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(1990)
Tetrahedron: Asymmetry
, vol.1
, pp. 793-800
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Danieli, B.1
Lesma, G.2
Mauro, M.3
Palmisano, G.4
Passarella, D.5
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24
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0000772914
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(a) Hughes, T. V.; Hammond, S. D.; Cava, M. P. J. Org. Chem. 1998, 63, 401-402.
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Hughes, T.V.1
Hammond, S.D.2
Cava, M.P.3
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25
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33846037921
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(b) Katritzky, A. R.; Akue-Gedu, R.; Vakulenko, A. V. ARKIVOC 2007, No. iii, 5-12.
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ARKIVOC
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Katritzky, A.R.1
Akue-Gedu, R.2
Vakulenko, A.V.3
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26
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0006911348
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(c) Katritzky, A. R.; Brzezinski, J. Z.; Lam, J. N. Rev. Roum. Chim. 1991, 36, 573-580.
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Katritzky, A.R.1
Brzezinski, J.Z.2
Lam, J.N.3
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27
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84863239678
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note
-
The structures of (+)-10, (-)-13, (-)-14, (+)-16, (-)-17, (-)-18, (+)-19, (+)-20, and totally synthetic scholarisine A (1) were confirmed by single-crystal X-ray analysis.
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28
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0027634446
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(a) Kasai, T.; Watanabe, H.; Mori, K. Bioorg. Med. Chem. 1993, 1, 67-70.
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Kasai, T.1
Watanabe, H.2
Mori, K.3
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30
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0000230330
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-
To our knowledge, this is the first example of such a cyclization. Rhodium on alumina has been shown to tolerate the oxirane moiety. See: (a)
-
To our knowledge, this is the first example of such a cyclization. Rhodium on alumina has been shown to tolerate the oxirane moiety. See: (a) Tarbell, D. S.; West, R. L.; McNally, J. G.; McCorkindale, N. J.; Kunstmann, M.; Carman, R. M.; Cremer, S. E.; Cross, A. D.; Huffman, K. R.; Varino, H. L.; Rosowsky, A.; Chapman, D. D. J. Am. Chem. Soc. 1961, 83, 3096-3113.
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West, R.L.2
McNally, J.G.3
McCorkindale, N.J.4
Kunstmann, M.5
Carman, R.M.6
Cremer, S.E.7
Cross, A.D.8
Huffman, K.R.9
Varino, H.L.10
Rosowsky, A.11
Chapman, D.D.12
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31
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0001329620
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Rhodium on alumina has also been shown to reduce nitriles preferentially to primary amines. See: (b)
-
Rhodium on alumina has also been shown to reduce nitriles preferentially to primary amines. See: (b) Freifelder, M. J. Am. Chem. Soc. 1960, 82, 2386-2389.
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J. Am. Chem. Soc.
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Freifelder, M.1
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32
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8744245263
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Bridged azapolycyclic alcohols have been synthesized via intramolecular expoxide opening by an amide. See: (c)
-
Bridged azapolycyclic alcohols have been synthesized via intramolecular expoxide opening by an amide. See: (c) Schultz, R.; Staas, W.; Spurlock, L. J. Org. Chem. 1973, 38, 3091-3093.
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J. Org. Chem.
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Schultz, R.1
Staas, W.2
Spurlock, L.3
-
34
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0015505219
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Our approach to the akuammiline-type alkaloids exploiting a Fischer indole synthesis with the 2-azabicyclo[3.3.1]nonan-8-one ring system was inspired by Dolby's pioneering efforts. See: (a)
-
Our approach to the akuammiline-type alkaloids exploiting a Fischer indole synthesis with the 2-azabicyclo[3.3.1]nonan-8-one ring system was inspired by Dolby's pioneering efforts. See: (a) Dolby, L. J.; Esfandiari, Z. J. Org. Chem. 1972, 37, 43-46.
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Dolby, L.J.1
Esfandiari, Z.2
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36
-
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19944414273
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Garg has also recently used this approach (see ref 11). We also note the work of Bosch. See: (c)
-
Garg has also recently used this approach (see ref 11). We also note the work of Bosch. See: (c) Bennasar, M. L.; Zulaica, E.; Lopez, M.; Bosch, J. Tetrahedron Lett. 1988, 29, 2361-2364.
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Bennasar, M.L.1
Zulaica, E.2
Lopez, M.3
Bosch, J.4
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38
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0029911562
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(e) Bennasar, M. L.; Zulaica, E.; Ramirez, A.; Bosch, J. J. Org. Chem. 1996, 61, 1239-1251.
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Bennasar, M.L.1
Zulaica, E.2
Ramirez, A.3
Bosch, J.4
-
41
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37049102588
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-
Benzoylphenylhydrazine also provided a stable hydrazone intermediate but led to the unprotected indole upon cyclization. See
-
Benzoylphenylhydrazine also provided a stable hydrazone intermediate but led to the unprotected indole upon cyclization. See: Mills, K.; Alkhawaja, K.; Alsaleh, F.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1981, 636-641.
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Mills, K.1
Alkhawaja, K.2
Alsaleh, F.3
Joule, J.A.4
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43
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0027997412
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Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666.
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Synthesis
, pp. 639-666
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Ley, S.V.1
Norman, J.2
Griffith, W.P.3
Marsden, S.P.4
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47
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0025737244
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(a) Watanabe, T.; Kobayashi, A.; Nishiura, M.; Takahashi, H.; Usui, T.; Kamiyama, I.; Mochizuki, N.; Noritake, K.; Yokoyama, Y.; Murakami, Y. Chem. Pharm. Bull. 1991, 39, 1152-1156.
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Watanabe, T.1
Kobayashi, A.2
Nishiura, M.3
Takahashi, H.4
Usui, T.5
Kamiyama, I.6
Mochizuki, N.7
Noritake, K.8
Yokoyama, Y.9
Murakami, Y.10
-
48
-
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0021177272
-
-
(b) Murakami, Y.; Watanabe, T.; Kobayashi, A.; Yokoyama, Y. Synthesis 1984, 738-740.
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(1984)
Synthesis
, pp. 738-740
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Murakami, Y.1
Watanabe, T.2
Kobayashi, A.3
Yokoyama, Y.4
-
50
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84888587878
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Schwesinger, R.; Willaredt, J.; Schlemper, H.; Keller, M.; Schmitt, D.; Fritz, H. Chem. Ber. 1994, 127, 2435-2454.
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Schwesinger, R.1
Willaredt, J.2
Schlemper, H.3
Keller, M.4
Schmitt, D.5
Fritz, H.6
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53
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84863235851
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-
note
-
The assignment of the absolute configuration of (+)-scholarisine A (1) was derived from the known absolute configurations of (-)-15 and (+)-20.
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