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J.-F. F. Weber, I. A. Wahab, A. Marzuki, N. A. Thomas, A. A. Kadir, A. H. A. Hadi, K. Awang, A. A. Latiff, P. Richomme, J. Delaunay, Tetrahedron Lett. 2001, 42, 4895-4897.
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E. H. Sahidin, L. D. Juliawaty, Y. M. Syah, L. Din, E. L. Ghisalberti, J. Latip, I. M. Said, S. A. Achman, Z. Naturforsch. C 2005, 60, 723-727.
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Ge, H.M.1
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5
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4644331452
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For an excellent review on total syntheses of colchicine
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For an excellent review on total syntheses of colchicine, see:, T. Graening, H.-G. Schmalz, Angew. Chem. 2004, 116, 3292-3318
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8
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Using thermodynamic strain energy to dictate synthetic planning is rare, though kinetic energies have been used to great effect with one example being calculation of atropisomeric equilibrations to determine the ordering of bond constructions for the vancomycin aglycon
-
Using thermodynamic strain energy to dictate synthetic planning is rare, though kinetic energies have been used to great effect with one example being calculation of atropisomeric equilibrations to determine the ordering of bond constructions for the vancomycin aglycon:, D. L. Boger, S. Miyazaki, S. H. Kim, J. H. Wu, S. L. Castle, O. Loiseleur, Q. Jin, J. Am. Chem. Soc. 1999, 121, 10004-10011.
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Boger, D.L.1
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9
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S. A. Snyder, A. L. Zografos, Y. Lin, Angew. Chem. 2007, 119, 8334-8339
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Snyder, S.A.1
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Angew. Chem. Int. Ed. 2007, 46, 8186-8191
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Angew. Chem. Int. Ed.
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11
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S. A. Snyder, S. P. Breazzano, A. G. Ross, Y. Lin, A. L. Zografos, J. Am. Chem. Soc. 2009, 131, 1753-1765.
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J. Am. Chem. Soc.
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Snyder, S.A.1
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Zografos, A.L.5
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12
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0034039459
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T. Tanaka, T. Ito, K. Nakaya, M. Iinuma, S. Riswan, Phytochemistry 2000, 54, 63-69.
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Phytochemistry
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Tanaka, T.1
Ito, T.2
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Riswan, S.5
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14
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0029040856
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S. E. Snyder, F. A. Aviles-Garay, R. Chakraborti, D. E. Nichols, V. J. Watts, R. B. Mailman, J. Med. Chem. 1995, 38, 2395-2409
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(1995)
J. Med. Chem.
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Snyder, S.E.1
Aviles-Garay, F.A.2
Chakraborti, R.3
Nichols, D.E.4
Watts, V.J.5
Mailman, R.B.6
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15
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0018858113
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N. J. Bach, E. C. Kornfeld, N. D. Jones, M. O. Chaney, D. E. Dorman, J. W. Paschal, J. A. Clemens, E. B. Smalstig, J. Med. Chem. 1980, 23, 481-491.
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J. Med. Chem.
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Bach, N.J.1
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Dorman, D.E.5
Paschal, J.W.6
Clemens, J.A.7
Smalstig, E.B.8
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17
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1242273629
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M. Curini, F. Epifano, M. C. Marcotullio, F. Montanari, Synlett 2004, 368-370
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Curini, M.1
Epifano, F.2
Marcotullio, M.C.3
Montanari, F.4
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19
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77957719306
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S. A. Snyder, D. S. Treitler, A. P. Brucks, J. Am. Chem. Soc. 2010, 132, 14303-14314.
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J. Am. Chem. Soc.
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Snyder, S.A.1
Treitler, D.S.2
Brucks, A.P.3
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20
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80052470241
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Intriguingly, use of either of these reagents separately did not afford the desired product
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Intriguingly, use of either of these reagents separately did not afford the desired product.
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-
-
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21
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80052450272
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-
It is worth noting that if 17 was first added to aldehyde 14, no attempt at subsequent haloetherification to reach 20 directly succeeded in any observable yield (although at best only 50 % of material could be advanced to the desired product due to the extra stereogenic center)
-
It is worth noting that if 17 was first added to aldehyde 14, no attempt at subsequent haloetherification to reach 20 directly succeeded in any observable yield (although at best only 50 % of material could be advanced to the desired product due to the extra stereogenic center).
-
-
-
-
22
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80052443508
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-
Earlier protection of the phenols as benzyl ethers prevented the smooth preparation of alcohol 13 because of issues of additional strain imparted by these groups in forging critical C-C bonds
-
Earlier protection of the phenols as benzyl ethers prevented the smooth preparation of alcohol 13 because of issues of additional strain imparted by these groups in forging critical C-C bonds.
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-
-
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23
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0027316023
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Y. Oshima, Y. Ueno, K. Hisamichi, M. Takeshita, Tetrahedron 1993, 49, 5801-5804
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(1993)
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0032145150
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T. Tanaka, M. Ohyama, K. Morimoto, F. Asai, M. Iinuma, Phytochemistry 1998, 48, 1241-1243
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Tanaka, T.1
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0034929480
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T. Tanaka, I. Iliya, T. Ito, M. Furusawa, K. Nakaya, M. Iinuma, Y. Shitataki, N. Matsuura, M. Ubukata, J. Murata, F. Simozono, K. Hirai, Chem. Pharm. Bull. 2001, 49, 858-862
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K.-S. Huang, Y.-H. Wang, R.-L. Li, M. Lin, J. Nat. Prod. 2000, 63, 86-89.
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Huang, K.-S.1
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57649171462
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S. S. Velu, I. Buniyamin, L. K. Ching, F. Feroz, I. Noorbatcha, L. C. Gee, K. Awang, I. B. Wahab, J.-F. F. Weber, Chem. Eur. J. 2008, 14, 11376-11384
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Chem. Eur. J.
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Velu, S.S.1
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77952048129
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W. Li, H. Li, Y. Luo, Y. Yang, N. Wang, Synlett 2010, 1247-1250.
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Synlett
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Li, W.1
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Wang, N.5
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29
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80052507446
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Conditions attempted included exposure to acid and heat, as well as the trityl cation to try and establish a dynamic equilibrium
-
Conditions attempted included exposure to acid and heat, as well as the trityl cation to try and establish a dynamic equilibrium.
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-
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30
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78650106876
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S. A. Snyder, T. C. Sherwood, A. G. Ross, Angew. Chem. 2010, 122, 5272-5276
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Angew. Chem.
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Sherwood, T.C.2
Ross, A.G.3
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(2010)
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, vol.49
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32
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77952873381
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For an excellent review on synthetic approaches to polyphenolic natural products in general
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K. C. Nicolaou, Q. Kang, T. R. Wu, C. S. Lim, D. Y.-K. Chen, J. Am. Chem. Soc. 2010, 132, 7540-7548. For an excellent review on synthetic approaches to polyphenolic natural products in general, see
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J. Am. Chem. Soc.
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Nicolaou, K.C.1
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S. Quideau, D. Deffieux, C. Douat-Casassus, L. Pouységu, Angew. Chem. 2011, 123, 610-646
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Angew. Chem.
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Pouységu, L.4
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34
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78651397186
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For recent work to prepare oligomeric polyphenols beyond the dimer level
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Angew. Chem. Int. Ed. 2011, 50, 586-621. For recent work to prepare oligomeric polyphenols beyond the dimer level, see
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Angew. Chem. Int. Ed.
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35
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S. A. Snyder, A. Gollner, M. I. Chiriac, Nature 2011, 474, 461-466
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(2011)
Nature
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Snyder, S.A.1
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80052490873
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K. Ohmori, T. Shono, Y. Hatakoshi, T. Yano, K. Suzuki, Angew. Chem. 2011, 123, 4964-4969
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Angew. Chem. Int. Ed. 2011, 50, 4862-4867.
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