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1
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31944441650
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Subsequent reports will describe the synthesis of the individual antipodes of garsubellin
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D. R. Siegel, S. J. Danishefsky, J. Am. Chem. Soc. 2006, 128, 1048. Subsequent reports will describe the synthesis of the individual antipodes of garsubellin.
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(2006)
J. Am. Chem. Soc
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Siegel, D.R.1
Danishefsky, S.J.2
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2
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26844495771
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For the first reported total syntheses of garsubellin, see
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For the first reported total syntheses of garsubellin, see A. Kuramochi, H. Usuda, K. Yamatsugu, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 14200.
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J. Am. Chem. Soc
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Kuramochi, A.1
Usuda, H.2
Yamatsugu, K.3
Kanai, M.4
Shibasaki, M.5
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3
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0035858503
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a) O. Cuesta-Rubio, H. Velez-Castro, B. A. Frontana-Uribe, J. Cardenas, Phytochemistry 2001, 57, 279:
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Phytochemistry
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Cuesta-Rubio, O.1
Velez-Castro, H.2
Frontana-Uribe, B.A.3
Cardenas, J.4
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5
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0036249452
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c) O. Cuesta-Rubio, B. A. Frontana-Uribe, T. Ramirez-Apan, J. Z. Cardenas, Z. Naturforsch. C 2002, 57, 372.
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Z. Naturforsch. C
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Cuesta-Rubio, O.1
Frontana-Uribe, B.A.2
Ramirez-Apan, T.3
Cardenas, J.Z.4
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6
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0000842321
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a) L. E. McCandlish, J. C. Hanson, G. H. Stout, Acta Crystallogr. Sect. B 1976, 32, 1793;
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Acta Crystallogr. Sect. B
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McCandlish, L.E.1
Hanson, J.C.2
Stout, G.H.3
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7
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22544485071
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b) A. L. Piccinelli, O. Cuesta-Rubio, M. B. Chica, N. Mahmood, B. Pagano, M. Pavone, V. Barone, L. Rastrelli, Tetrahedron 2005, 61, 8206-8211.
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Tetrahedron
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Piccinelli, A.L.1
Cuesta-Rubio, O.2
Chica, M.B.3
Mahmood, N.4
Pagano, B.5
Pavone, M.6
Barone, V.7
Rastrelli, L.8
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8
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33845249441
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A total synthesis of clusianone has recently appeared, see a
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A total synthesis of clusianone has recently appeared, see a) V. Rodeschini, N. M. Ahmad, N. S. Simpkins, Org. Lett. 2006, 8, 5283;
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(2006)
Org. Lett
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Rodeschini, V.1
Ahmad, N.M.2
Simpkins, N.S.3
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9
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34250836871
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b) N. M. Ahmad, V. Rodeschini, N. S. Simpkins, S. E. Ward, A. J. Blake, J. Org. Chem. 2007, 72, 4803;
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J. Org. Chem
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Ahmad, N.M.1
Rodeschini, V.2
Simpkins, N.S.3
Ward, S.E.4
Blake, A.J.5
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10
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33846570462
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The steps which we employed were actually done independently before the appearance of the above report
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c) P. Nuhant, M. David, T. Pouplin, B. Delpech, C. Marazano, Org. Lett. 2007, 9, 287. The steps which we employed were actually done independently before the appearance of the above report.
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Org. Lett
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Nuhant, P.1
David, M.2
Pouplin, T.3
Delpech, B.4
Marazano, C.5
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11
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0001663295
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T. Satoh, M. Ikeda, M. Miura, M. Nomura, J. Org. Chem. 1997, 62, 4877.
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Satoh, T.1
Ikeda, M.2
Miura, M.3
Nomura, M.4
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12
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36749016657
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Attempts to execute the cross-metathesis with 2-methyl-2-butene resulted in formation of significant amounts of a disubstituted olefin side product. To avoid this undesired side reaction, 2-methylpropene was used in the cross-metathesis reaction;
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a) Attempts to execute the cross-metathesis with 2-methyl-2-butene resulted in formation of significant amounts of a disubstituted olefin side product. To avoid this undesired side reaction, 2-methylpropene was used in the cross-metathesis reaction;
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13
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0001754263
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b) A. K. Chatterjee, D. P. Sanders, R. H. Grubbs, Org. Lett. 2002, 4, 1939;
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Org. Lett
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Chatterjee, A.K.1
Sanders, D.P.2
Grubbs, R.H.3
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15
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33947093954
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A. P. Krapcho, J. F. Weimaster, J. M. Eldridge, E. G. E., Jr. Jahngen, A. J. Lovey, W. P. Stephens, J. Org. Chem. 1978, 43, 138.
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J. Org. Chem
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Krapcho, A.P.1
Weimaster, J.F.2
Eldridge, J.M.3
Jahngen Jr., E.G.E.4
Lovey, A.J.5
Stephens, W.P.6
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19
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0033583729
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For the earliest reported type of reaction in this general area, see a
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For the earliest reported type of reaction in this general area, see a) K. C. Nicolaou, J. A. Pfefferkorn, S. Kim, H. X. Wei, J. Am. Chem. Soc. 1999, 121, 4724;
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J. Am. Chem. Soc
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Nicolaou, K.C.1
Pfefferkorn, J.A.2
Kim, S.3
Wei, H.X.4
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20
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0001027385
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b) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, S. Kim, J. Kessabi, Org. Lett. 1999, 1, 807.
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Nicolaou, K.C.1
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Kim, S.4
Kessabi, J.5
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22
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36749035266
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It seems reasonable to assume that introduction of deuterium at the bridgehead is indicative of bridgehead deprotonation by the LDA. The alternative would be that the actual removal of the proton at C1 is somehow occurring during the CD3OD quenching process via some combination of secondary amine and secondary lithium amide
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3OD quenching process via some combination of secondary amine and secondary lithium amide.
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23
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0000332522
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cf. inter alia; a N. G. Clemo and G. Pattenden, Tetrahedron Lett. 1982, 23, 585;
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cf. inter alia; a) N. G. Clemo and G. Pattenden, Tetrahedron Lett. 1982, 23, 585;
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27
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36749026517
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see reference [5
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d) see reference [5].
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28
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36749103117
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At several stages of this study, the apparent deprotonation [13] and subsequent quenching of the bridgehead enolate with electrophiles is improved through the use of TMSCl. The reasons for this remain to be explored in detail
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[13] and subsequent quenching of the bridgehead enolate with electrophiles is improved through the use of TMSCl. The reasons for this remain to be explored in detail.
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30
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0001484561
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b) L. T. Scott, K. J. Carlin, T. H. Schultz, Tetrahedron Lett. 1978, 19, 4637;
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Tetrahedron Lett
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Scott, L.T.1
Carlin, K.J.2
Schultz, T.H.3
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32
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0001553502
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B. H. Lipshutz, M. Koerner, D. A. Parker, Tetrahedron Lett. 1987, 28, 945.
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Tetrahedron Lett
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Lipshutz, B.H.1
Koerner, M.2
Parker, D.A.3
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33
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36749003724
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With nemorosone in hand, we found that it was both light-sensitive and air-sensitive. When nemorosone was dissolved in chloroform, a solution of fully synthetic nemorosone and chloroform had decomposed after a few days at room temperature. In fact, a solution of nemorosone in chloroform at -20°C is also significantly decomposed after a few days. We resorted to the use of ammonium formate because the original isolation was such that ammonium formate would have been present in the methanol solvent wherein the NMR spectrum of nemorosone was measured. Through this device, a stable spectrum was obtained
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With nemorosone in hand, we found that it was both light-sensitive and air-sensitive. When nemorosone was dissolved in chloroform, a solution of fully synthetic nemorosone and chloroform had decomposed after a few days at room temperature. In fact, a solution of nemorosone in chloroform at -20°C is also significantly decomposed after a few days. We resorted to the use of ammonium formate because the original isolation was such that ammonium formate would have been present in the methanol solvent wherein the NMR spectrum of nemorosone was measured. Through this device, a stable spectrum was obtained.
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34
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36749044727
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In addition to the proton spectrum, a 13C spectrum was also obtained on fully synthetic nemorosone. Infrared and mass spectra were all measured. These data are found in the Supporting Information
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13C spectrum was also obtained on fully synthetic nemorosone. Infrared and mass spectra were all measured. These data are found in the Supporting Information.
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35
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0001434093
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K. Miura, Y. Ichinose, K. Nozaki, K. Fugami, K. Oshima and K. Utimoto, Bull. Chem. Soc. Jpn. 1989, 62, 143.
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Bull. Chem. Soc. Jpn
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Miura, K.1
Ichinose, Y.2
Nozaki, K.3
Fugami, K.4
Oshima, K.5
Utimoto, K.6
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