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28044439926
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New York, Sept 7-11, 2003; American Chemical Society. Washington, DC
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(b) For another attempted synthesis, see: Wu, T.; Kraus, G. Abstracts of Papers; 226th National Meeting of the American Chemical Society, New York, Sept 7-11, 2003; American Chemical Society. Washington, DC, 2003.
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Wu, T.1
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5
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0000169302
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For another synthesis of this tri cyclic ring system, see: Hegedus, L. S.; Sestrick, M. R.; Michaelson, E. T.; Harrington, P. J. J. Org. Chem. 1989, 54, 4141.
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9
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28044444942
-
-
note
-
2, further substitution occurred in the 8-position.
-
-
-
-
10
-
-
28044455067
-
-
note
-
2 proved difficult and time-consuming on a large scale.
-
-
-
-
11
-
-
0012458225
-
-
3-catalyzed aromatic substitution, see: (a) DeHaan, F. P.; Covey, W. D.; Delker, G. L.; Baker, N. J.; Feigon, J. F.; Ono, D.; Miller, K. D.; Stelter, E. D. J. Org. Chem. 1984, 49, 3959.
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Delker, G.L.3
Baker, N.J.4
Feigon, J.F.5
Ono, D.6
Miller, K.D.7
Stelter, E.D.8
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12
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5344266024
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(b) DeHaan, F. P.; Delker, G. L.; Covey, W. D.; Bellomo, A. F.; Brown, J. A.; Ferrara, D. M.; Haubrich, R. H.; Lander, E. B.; MacArthur, C. J.; Meinhold, R. W.; Neddenriep, D.; Schubert, D. M.; Stewart, R. G. J. Org. Chem. 1984, 49, 3963.
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Brown, J.A.5
Ferrara, D.M.6
Haubrich, R.H.7
Lander, E.B.8
MacArthur, C.J.9
Meinhold, R.W.10
Neddenriep, D.11
Schubert, D.M.12
Stewart, R.G.13
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13
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1542473694
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(c) Covey, W. D.; DeHaan, F. P.; Delker, G. L.; Dawson, S. F.; Kilpatrick, P. K.; Rattinger, G. B.; Read, W. G. J. Org. Chem. 1984, 49, 3967.
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Covey, W.D.1
DeHaan, F.P.2
Delker, G.L.3
Dawson, S.F.4
Kilpatrick, P.K.5
Rattinger, G.B.6
Read, W.G.7
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14
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28044467188
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-
note
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3N or Hunig's base led to acylation at the phenol. Schotten-Baumann conditions also proved ineffective in completing this transformation.
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-
-
-
17
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0342626647
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(c) Epsztajn, J.; Jóźwiak, A.; Kołuda, P.; Sadokierska, I.; Wilkowska, I. D. Tetrahedron 2000, 56, 4837.
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Epsztajn, J.1
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Wilkowska, I.D.5
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18
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0005827026
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Swenton, J. S.; Bonke, B. R.; Chen, C. P.; Chou, C. T. J. Org. Chem. 1989, 54, 51.
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19
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Mizutani, T.; Honzawa, S.; Tosaki, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 4680.
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Mizutani, T.1
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22
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0003961355
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Regioselective synthesis of organolithiums by deprotonation
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Tetrahedron Organic Chemistry Series; Elsevier Science: London, Chapt. 2
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(a) Clayden, J. Regioselective Synthesis of Organolithiums by Deprotonation. In Organolithiums: Selectivity for Synthesis; Tetrahedron Organic Chemistry Series; Elsevier Science: London, 2002; Vol. 23, Chapt. 2, pp 30-31.
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Organolithiums: Selectivity for Synthesis
, vol.23
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Clayden, J.1
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25
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28044450453
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note
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1H NMR spectrum.
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-
-
-
26
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33845183730
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Mills, R. J.; Taylor, N. J.; Snieckus, V. J. Org. Chem. 1989, 54, 4372.
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Mills, R.J.1
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Snieckus, V.3
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28
-
-
28044462260
-
-
note
-
Only silyl-based protecting groups could be successfully introduced on the phenol after the bromination reaction. Various benzyl groups were attempted, but all led to either recovered starting material or low yields.
-
-
-
-
29
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28044440741
-
-
note
-
2O and deuterium failed to incorporate into the ring system.
-
-
-
-
30
-
-
0011787127
-
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For other examples of where this has been necessary, see: (a) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072.
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(b) Kelly, T. R.; Silva, R. A.; De Silva, H.; Jasmin, S.; Zhao, Y. J. Am. Chem. Soc. 2000, 122, 6935.
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0003961355
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Regioselective synthesis of organolithiums by X-Li exchange
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Tetrahedron Organic Chemistry Series; Elsevier Science: London, Chapt. 3
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For a discussion on the kinetics of halogen-lithium exchange, see: Clayden, J. Regioselective Synthesis of Organolithiums by X-Li Exchange. In Organolithiums: Selectivity for Synthesis; Tetrahedron Organic Chemistry Series; Elsevier Science: London, 2002; Chapt. 3, pp 116-117.
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Clayden, J.1
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33
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28044453798
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Rearrangement reactions with migration of silicon
-
Butterworth Monographs in Chemistry and Chemical Engineering; Butterworth: London
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For discussions of silicon group migrations, see: (a) Colvin, E. Rearrangement reactions with migration of silicon. In Silicon in Organic Synthesis; Butterworth Monographs in Chemistry and Chemical Engineering; Butterworth: London, 1981; pp 30-39.
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Colvin, E.1
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0003961355
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Organolithium rearrangements
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Tetrahedron Organic Chemistry Series; Elsevier Science: London, Chapt. 8
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(c) Clayden, J. Organolithium Rearrangements. In Organolithiums: Selectivity for Synthesis; Tetrahedron Organic Chemistry Series; Elsevier Science: London, 2002; Chapt. 8, pp 340-346.
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, pp. 340-346
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-
Clayden, J.1
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37
-
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28044434472
-
-
note
-
This temperature is extremely important for the success of the transformation. Running the reaction at slightly higher (0 °C) or lower (-20 °C) temperatures resulted in incomplete lithiation.
-
-
-
-
38
-
-
28044435674
-
-
note
-
Presumably due to the base-induced decomposition of ethyl formate, DMF (when used as the aldehyde source), or THF.
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-
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-
39
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0030576868
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van Heerden, P. S.; Bezuidenhoudt, B. C. B.; Ferreira, D. Tetrahedron 1996, 52, 12313.
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6244279150
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For discussions and examples where TMSC1 has been used to accelerate the conjugate addition of organocopper and organocuprate reagents, see: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015.
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(c) Horiguchi, Y.; Matsuzawa, S.; Nadamura, E.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 4025.
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0032535180
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47
-
-
28044460653
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note
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Running this reaction in DMF, DMSO, or THF resulted in only recovered starting material.
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-
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51
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85002822844
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(d) Tamura, Y.; Yoshimoto, Y.; Sakai, K.; Kita, Y. Synthesis 1980, 483.
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28044469359
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Neutral conditions: (a) Weidner, J. J.; Weintraub, P. M.; Schnettler, R. A.; Peet, N. P. Tetrahedron 1997, 53, 6303.
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0038682516
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(b) Smith, A. B., III; Kanoh, N.; Ishiyama, H.; Minakawa, N.; Rainier, J. D.; Hartz, R. A.; Cho, Y. S.; Cui, H.; Moser, W. H. J. Am. Chem. Soc. 2003, 125, 8228.
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57
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28044446830
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note
-
Inferior yields were obtained with LiOH, NaOH, or CsOH. The use of other alcohols (i.e., EtOH, 'PrOH, "BuOH) as solvent also resulted in a reduction in yield.
-
-
-
-
58
-
-
28044450935
-
-
note
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All attempts at applying the chemistry that afforded 11 to desmethyl derivatives of 59 were met with failure.
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-
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59
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0001491460
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Metallinos, C.; Nerdinger, S.; Snieckus, V. Org. Lett. 1999, 1, 1183.
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84982341931
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For reviews of amide/lactam acetal formation, see: (a) Meerwein, v. H.; Florian, W.; Schön, N.; Stopp, G. Justus Liebigs Ann. Chem. 1961, 641, 1.
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Meerwein, V.H.1
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0002474959
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For related transformations that result in amide cleavage, see: (a) Charette, A. B.; Chua, P. Synlett 1998, 163.
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Charette, A.B.1
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(b) Keck, G. E.; McLaws, M. D.; Wager, T. T. Tetrahedron 2000, 56, 9875.
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Keck, G.E.1
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Wager, T.T.3
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65
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28044455287
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note
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Attempts to isolate the immonium intermediate in dry form and then treat it with methoxide in MeOH also failed.
-
-
-
-
68
-
-
28044442784
-
-
note
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See Supporting Information for general experimental procedures.
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