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1
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0001562822
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For leading references see: (a)
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For leading references see: (a) Hart, D.J. Science 1984, 223, 883.
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Science
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Hart, D.J.1
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9
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0000751449
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(d)
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(d) RajanBabu, T.V.; Fukunaga, T.; Reddy, G.S. J. Am. Soc. 1989, 111, 1759.
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J. Am. Soc.
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Rajanbabu, T.V.1
Fukunaga, T.2
Reddy, G.S.3
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13
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0000896969
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(h)
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(h) Marco-Contelles, J.; Ruiz-Fernandez, P.; Sanchez, B. J. Org. Chem. 1993, 58, 2894.
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Marco-Contelles, J.1
Ruiz-Fernandez, P.2
Sanchez, B.3
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14
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0342323989
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(a)
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(a) Wayner, D.D.M.; Abey Chatgilialoglu, C.; Ingold, K.U.; Scaiano, J.C. J. Am. Soc. 1981, 103, 7739.
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J. Am. Soc.
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Wayner, D.D.M.1
Abey Chatgilialoglu, C.2
Ingold, K.U.3
Scaiano, J.C.4
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15
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0001259279
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(b)
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(b) Lusztyh, J.; Maillard, B.; Lindsay, D.A.; Ingold, K.U. J. Am. Chem. Soc. 1983, 105, 3578.
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Lusztyh, J.1
Maillard, B.2
Lindsay, D.A.3
Ingold, K.U.4
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16
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0001360724
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(c)
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(c) Johnston, L.J.; Lusztyk, J.; Wichreyma, A.N.; Beckwith, A.L.J.; Scaiano, J.C.; Ingold, K.V. J. Am. Chem. Soc. 1985, 107, 4594.
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Johnston, L.J.1
Lusztyk, J.2
Wichreyma, A.N.3
Beckwith, A.L.J.4
Scaiano, J.C.5
Ingold, K.V.6
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19
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33748244854
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De Armas P., Francisco C.G., Suarez E.
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de Armas, P.; Francisco, C.G.; Suarez, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 772.
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20
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(b) de Armas, P.; Francisco, C.G.; Suarez, E. J. Am. Chem. Soc. 1993, 115, 8865.
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Francisco, C.G.2
Suarez, E.3
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21
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(c)
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(c) de Armas, P.; Francisco, C.G.; Suarez, E. Tetrahedron Lett. 1993, 34, 7331.
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Tetrahedron Lett.
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De Armas, P.1
Francisco, C.G.2
Suarez, E.3
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22
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0342758817
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In the case of entry 1 () the crude reaction mixture was chromatographed on silica gel, although the cyclic iodine was unstable on chromatography we obtained enough amounts to be identified
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In the case of entry 1 ( ) the crude reaction mixture was chromatographed on silica gel, although the cyclic iodine was unstable on chromatography we obtained enough amounts to be identified.
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23
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0342323983
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The following procedure is typical for the synthesis of 2: a solution of carbohydrate 1 (100 mg, 0.273 mmol) in dry benzene (8 ml) containing iodosylbenzene (180 mg, 0.819 mmol) and iodine (69 mg, 0.273 mmol) was desoxigenated by three cycles of freeze-pump-taw. The solution, under nitrogen, was refluxed for 3h. The reaction mixture was then poured into water and extracted with ether. The organic layer was washed with aqueous sodium thiosulfate and water. To the crude reaction mixture in benzene (3 ml) was added a spatula tip of AIBN and tri-Phenyltin hydride (0.084 ml, 0.33 mmol). This mixture was heated at reflux for 4h. Concentration and purification by flash chromatography (benzene/ethyl acetate 80:20 v/v) gave (40mg, 41%)
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The following procedure is typical for the synthesis of 2: a solution of carbohydrate 1 (100 mg, 0.273 mmol) in dry benzene (8 ml) containing iodosylbenzene (180 mg, 0.819 mmol) and iodine (69 mg, 0.273 mmol) was desoxigenated by three cycles of freeze-pump-taw. The solution, under nitrogen, was refluxed for 3h. The reaction mixture was then poured into water and extracted with ether. The organic layer was washed with aqueous sodium thiosulfate and water. To the crude reaction mixture in benzene (3 ml) was added a spatula tip of AIBN and tri-Phenyltin hydride (0.084 ml, 0.33 mmol). This mixture was heated at reflux for 4h. Concentration and purification by flash chromatography (benzene/ethyl acetate 80:20 v/v) gave (40mg, 41%).
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25
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0000751449
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(b)
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(b) RajanBabu, T.V.; Fukunaga, T.V.; Reddy, G.S. J. Am. Chem. Soc. 1989, 111, 1759.
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(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 1759
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Rajanbabu, T.V.1
Fukunaga, T.V.2
Reddy, G.S.3
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26
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0343193428
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Beckwith, A.L.J.; Pigou, P.E. J. Chem. Soc., Chem. Commun. 1986, 54, 3140.
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(1986)
J. Chem. Soc., Chem. Commun.
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Beckwith, A.L.J.1
Pigou, P.E.2
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28
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0024809070
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(c)
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(c) Oumar-Mahamat, H.; Moustrou, C.; Surzur, J.M.; Bertran, M.P. J. Org. Chem. 1989, 54, 5684.
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Oumar-Mahamat, H.1
Moustrou, C.2
Surzur, J.M.3
Bertran, M.P.4
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29
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0025275785
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(d)
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(d) Nagashima, H.; Soki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo, Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985.
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J. Org. Chem.
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Nagashima, H.1
Soki, K.2
Ozaki, N.3
Wakamatsu, H.4
Itoh, K.5
Tomo, Y.6
Tsuji, J.7
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30
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33751553881
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(e)
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(e) Kates, A.; Dombroski, M.A.; Snider, B.B. J. Org. Chem. 1990, 56, 2427.
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J. Org. Chem.
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Kates, A.1
Dombroski, M.A.2
Snider, B.B.3
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32
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0342323981
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For oxidation of stabilized tertiary radical involved iodine see: b
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For oxidation of stabilized tertiary radical involved iodine see: b.
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