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14
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0001564960
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Several groups including our own have developed protocols for the acid-catalyzed furanosylation of an indolocarbazole nucleus using C2′ unsubstituted carbohydrate moieties. (a) Weinreb, S. M.; Garigipati, R. S.; Gainor, J. A. Heterocycles 1984, 21, 309.
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17
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0033518872
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For the rhodium-carbenoid initiated Claisen rearrangement, see: (a) Wood, J. L.; Moniz, G. A.; Pflum, D. A.; Stoltz, B. M.; Holubec, A. A.; Dietrich, H.-J. J. Am. Chem. Soc. 1999, 121, 1748.
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Dietrich, H.-J.J.6
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19
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0042706773
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note
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6,10
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20
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0000096885
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Montero, J.-L.4
Lucas, M.5
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21
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0041705148
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-
note
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We found that our stereochemical assignment of 6 was correct as 9 possessed the anticipated relative configuration between C2′ and C3′ (numbering based on K252a carbohydrate).
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-
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22
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33847800152
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Grieco, P. A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485.
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25
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Wood, J. L.; Stoltz, B. M.; Goodman, S. N.; Onwueme, K. J. Am. Chem. Soc. 1997, 119, 9652.
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-
26
-
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0042706772
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-
note
-
A considerable amount of benzylated 14 (at both indole nitrogens and as a mixture around the aromatic rings) was detected, accounting for the reduced yields when using 8.
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-
-
-
27
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0042205660
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note
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Further, 17-19 were rigorously chemically correlated to 16. The chemical correlation parallels the furanose interconversions illustrated in Scheme 1 and is detailed in the Supporting Information.
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28
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17344374130
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(a) Maroney, A. C.; Glicksman, M. A.; Basma, A. N.; Walton, K. M.; Knight, E., Jr.; Murphy, C. A.; Bartlett, B. A.; Finn, J. P.; Angeles, T.; Matsuda, Y.; Neff, N. T.; Dionne, C. A. J. Neurosci. 1998, 18, 104.
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Bartlett, B.A.7
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Angeles, T.9
Matsuda, Y.10
Neff, N.T.11
Dionne, C.A.12
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29
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0023155966
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(b) Kase, H.; Iwahashi, K.; Nakanishi, S.; Matsuda, Y.; Yamada, K.; Takahashi, M.; Murakata, C.; Sato, A.; Kaneko, M. Biochem. Biophys. Res. Comm. 1987, 142, 436.
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Murakata, C.7
Sato, A.8
Kaneko, M.9
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