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8
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0000541751
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Most recent colchicine syntheses: (a) Banwell, M. G. Pure Appl. Chem. 1996, 68, 539.
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For a recent review on the total synthesis of colchicine, see: (c) Graening, T.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2004, 43, 3230.
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12
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0036322149
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The intention to apply the same strategy for a colchicine total synthesis was put forward after our first disclosure: McMills, M.; Wright, D. L.; Weekly, R. M. Synth. Commun. 2002, 32, 2417.
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15
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26444593090
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note
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Attempts to utilize an aryllithium species derived from 9 by treatment with BuLi failed due to deprotonation at the propargylic stereocenter (intramolecular proton transfer).
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17
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26444456730
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note
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Diacel Chiralpak AD-H, hexane/i-PrOH = 9:1.
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18
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0025108625
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(a) Padwa, A.; Fryxell, G. E.; Zhi, L. J. Am. Chem. Soc. 1990, 112, 3100.
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(b) Padwa, A.; Chinn, R. L.; Hornbuckle, S. F.; Zhang, Z. J. J. Org. Chem. 1991, 56, 3271.
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21
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33751391278
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4, PhH, rt), compound 11 only afforded a dihydropyranone side-product resulting from 1,4 H-shift of the reactive intermediate 3. A similar side-product has been observed by Padwa in the reaction of a simple model compound. See: Padwa, A.; Hornbuckle, S. F.; Fryxell, G. E.; Zhang, Z. J. J. Org. Chem. 1992, 57, 5747.
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Padwa, A.1
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23
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0033576438
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See also: (b) Baldwin, J. E.; Mayweg, A. V. W.; Neumann, K.; Prithard, G. J. Org. Lett. 1999, 1, 1933.
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Baldwin, J.E.1
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24
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0003075009
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For a review on ring opening reactions in oxabicyclic ring systems, see: (c) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 1.
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25
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26444571006
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note
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The cleavage of the benzylic C-O bond should also be stereoelectronically assisted as the oxa-bridge is aligned with the π-system of the aromatic ring.
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26
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26444435451
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note
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Compound 16 also proved to be rather sensitive toward decomposition and was usually directly further oxidized to the tropolone 23 (Scheme 4).
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31
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0038742052
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(a) Baldwin, J. E.; Mayweg, A. v. W.; Pritchard, G. J.; Adlington, R. M. Tetrahedron Lett. 2003, 44, 4543.
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Banwell, M.G.1
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Greenwood, R.J.4
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34
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26444517890
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see ref 1a
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-1. For details, see ref 1a.
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