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5
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10744221306
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(d) Polla, M. O.; Tottie. L.; Norden, C.; Linschoten. M.; Müsil, M.: TrumppKallmeyer, S.; Aurkurst, I. R.: Ringom, R.; Holm, K. H.; Neset. S. M.; Sandberg, M.; Thurmond, J.: Yu, P.; Hategan. G.: Anderson, H. Biore. Med. Chem. 2004, 12, 1151-1175.
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Polla, M.O.1
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Müsil, M.5
TrumppKallmeyer, S.6
Aurkurst, I.R.7
Ringom, R.8
Holm, K.H.9
Neset, S.M.10
Sandberg, M.11
Thurmond, J.12
Yu, P.13
Hategan, G.14
Anderson, H.15
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Taniguchi, T.; Martin, C. L.; Monde, K.; Nakanishi, K.; Berova, N.; Overman, L. E. J. Nat. Prod. 2009, 72, 430-432.
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Taniguchi, T.1
Martin, C.L.2
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Nakanishi, K.4
Berova, N.5
Overman, L.E.6
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8
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45249090324
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For an account of this elegant approach, see
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For an account of this elegant approach, see: Martin, C. L.: Overman. L. E.: Rohde, J. M. J. Am. Chem. Soc. 2008, 130, 7568-7569.
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Martin, C.L.1
Overman, L.E.2
Rohde, J.M.3
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9
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0026570662
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For examples of amine trapping of indole-quinonemethide species, see: (a)
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For examples of amine trapping of indole-quinonemethide species, see: (a) Magnus, P.; Sear, N. L.: Kim, C. S.: Vicker. N. J. Org. Chem. 1992, 57. 70-78.
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Magnus, P.1
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Kim, C.S.3
Vicker, N.4
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10
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4544269722
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(b) Ohshima, T.; Xu, Y.; Takita. R.; Shibasaki. M. Tetrahedron 2004, 60, 9569-9588.
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Ohshima, T.1
Xu, Y.2
Takita, R.3
Shibasaki, M.4
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11
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0034034225
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(c) Ohori, K.; Shimizu, S.; Ohshima, T.; Shibasaki. M. Chirality 2000, 12, 400-403.
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Ohori, K.1
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Chirality, S.M.4
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12
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33645474138
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Nicolaou, K. C.; Lizos, D. E.: Kim, D. W.; Schlawe, D.; de Noronha, R. G.: Longbottom, D. A.; Rodriquez, M.; Bucci, M.: Cirino, G. J. Am. Chem. Soc. 2006, 128, 4460-4470.
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Nicolaou, K.C.1
Lizos, D.E.2
Kim, D.W.3
Schlawe, D.4
De Noronha, R.G.5
Longbottom, D.A.6
Rodriquez, M.7
Bucci, M.8
Cirino, G.9
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14
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1842483218
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For a review on enyne cross-metathesis, see
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For a review on enyne cross-metathesis, see: Diver, S. T.; Giessert, A. Chem. Rev. 2004, 104, 1317-1382.
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Chem. Rev.
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Diver, S.T.1
Giessert, A.2
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15
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70349900597
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Importantly, bromo diene 8 was produced in 60%-80% yield with exclusive frans-olefin selectivity under these reaction conditions
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Importantly, bromo diene 8 was produced in 60%-80% yield with exclusive frans-olefin selectivity under these reaction conditions.
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16
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0000068950
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Amine displacement of homoallylic dienyl bromide was adapted from
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Amine displacement of homoallylic dienyl bromide was adapted from: Arnold, H.; Overman. L. E.; Sharp, M. J.; Witschel, M. C. Org. Synth. 1992, 70, 111-118.
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Org. Synth.
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Arnold, H.1
Overman, L.E.2
Sharp, M.J.3
Witschel, M.C.4
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17
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0000698918
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Baum, J. S.: Shook, D. A.: Davies, H. M. L.: Smith, D. Synth. Commun. 1987, 17. 1709-1716.
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Synth. Commun.
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Baum, J.S.1
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Davies, H.M.L.3
Smith, D.4
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18
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0028230701
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For studies on the cyclopropanation of diazoacetamides. see: (a) Doyle, M. P.: Eismont. M. Y.; Protopopova, M. N.; Kwan, M. M. Y.
-
For studies on the cyclopropanation of diazoacetamides. see: (a) Doyle, M. P.: Eismont. M. Y.; Protopopova, M. N.; Kwan, M. M. Y. Tetrahedron 1994, 50, 1665-1674.
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(1994)
Tetrahedron
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19
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0001080522
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(b) Doyle, M. P; Austin. R. E.; Bailey. A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.: Kwan, M. M. Y.: Liras, S.; Oalmann, C. J.: Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H. P.; Zhou. Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763-5775.
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Doyle, M.P.1
Austin, R.E.2
Bailey, A.S.3
Dwyer, M.P.4
Dyatkin, A.B.5
Kalinin, A.V.6
Kwan, M.M.Y.7
Liras, S.8
Oalmann, C.J.9
Pieters, R.J.10
Protopopova, M.N.11
Raab, C.E.12
Roos, G.H.P.13
Zhou, Q.-L.14
Martin, S.F.15
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20
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0001155757
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For synthesis of Cu(TBS), see: Charles, R. G.
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For synthesis of Cu(TBS), see: Charles, R. G. J. Org. Chem. 1957, 22, 677-679.
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J. Org. Chem.
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21
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70349934622
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note
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Under these conditions only minimal quantities of side products were observed.
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22
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70349907840
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note
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These conditions remain unoptimized, and current efforts are focusing on both improving efficiency and utilizing chiral metal catalysts to induce asymmetry.
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24
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0029937878
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(b) Kobayashi, M.; Masumoto, K.; Nakai, E.: Nakai, T. Tetrahedron Lett. 1996, 37, 3005-3008.
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Tetrahedron Lett.
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Kobayashi, M.1
Masumoto, K.2
Nakai, E.3
Nakai, T.4
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25
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85077890350
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For a review on the use enoxysilane formation with silyl triflates. see
-
For a review on the use enoxysilane formation with silyl triflates. see: Emde, H.: Domsch. D.; Feger, H.; Frick, U.: Götz, A.: Hergott, H. H.; Hofmann, K.; Kober. W.: Krägeloh. K.; Oesterle, T.: Steppan, W.; West, W.; Simchen, G. Synthesis 1982, 1-26.
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(1982)
Synthesis
, pp. 1-26
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Emde, H.1
Domsch, D.2
Feger, H.3
Frick, U.4
Götz, A.5
Hergott, H.H.6
Hofmann, K.7
Kober, W.8
Krägeloh, K.9
Oesterle, T.10
Steppan, W.11
West, W.12
Simchen, G.13
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26
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0345308896
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For some examples of enoxysilane-mediated divinylcyclopropane rearrangement in the synthesis of functionalized cycloheptene rings, see: (a)
-
For some examples of enoxysilane-mediated divinylcyclopropane rearrangement in the synthesis of functionalized cycloheptene rings, see: (a) Piers, E.: Burmeister, M. S.: Reissig. H.-U. Can. J. Chem. 1986, 64. 180-187.
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Can. J. Chem.
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Piers, E.1
Burmeister, M.S.2
Reissig, H.-U.3
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30
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0033575122
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(e) Fox, M. E.: Li, C.; Marino, J. P.. Jr.: Overman, L. E. J. Am. Chem. Soc. 1999. 121, 5467-5480.
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J. Am. Chem. Soc.
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Fox, M.E.1
Li, C.2
Marino Jr., J.P.3
Overman, L.E.4
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31
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0000423379
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(a) Tsuji, J.: Shimizu, I.: Minami, I.; Ohashi, Y. Tetrahedron Lett. 1982, 23, 4809-4812.
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Tetrahedron Lett.
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Tsuji, J.1
Shimizu, I.2
Minami, I.3
Ohashi, Y.4
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32
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84990085666
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For a review of palladium-catalyzed allylic alkylations. see: (a)
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For a review of palladium-catalyzed allylic alkylations. see: (a) Trost. B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173-1192.
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Angew. Chem., Int. Ed. Engl.
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Trost, B.M.1
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33
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0346602829
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(b) Tsuji, J. Tetrahedron 1986. 42, 4361-4401.
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(1986)
Tetrahedron
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Tsuji, J.1
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34
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70349929393
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note
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Initial attempts to employ Phenylhydrazine hydrochloride in the Fischer indolization reaction of substrate 15 led to mixtures of products, which arose from non-deprotected and deprotection of the silyl ether.
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-
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35
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70349921180
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Attempts to condense Phenylhydrazine with ketone 15 under either neutral or protic acid conditions provided only low conversions to the desired hydrazone 19.
-
Attempts to condense Phenylhydrazine with ketone 15 under either neutral or protic acid conditions provided only low conversions to the desired hydrazone 19.
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36
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2342460927
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For examples of the use of Sc(OTf)3 as a Lewis acid activator for aldehydes in the presence of hydrazines, see: (a)
-
For examples of the use of Sc(OTf)3 as a Lewis acid activator for aldehydes in the presence of hydrazines, see: (a) Furrow. M. E.; Myers, A. G. J. Am. Chem. Soc. 2004, 126, 5436-5445.
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J. Am. Chem. Soc.
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Furrow, M.E.1
Myers, A.G.2
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38
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70349897556
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1H NMR analysis of the unpurified reaction mixture. Isolation yields of 19 typically ranged between 84%-97% yield
-
1H NMR analysis of the unpurified reaction mixture. Isolation yields of 19 typically ranged between 84%-97% yield,
-
-
-
-
39
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70349934612
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The configuration of hydrazone 19 (i.e., E-hydrazone vs. Zhydrazone) could not be determined by NMR
-
The configuration of hydrazone 19 (i.e., E-hydrazone vs. Zhydrazone) could not be determined by NMR.
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