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1
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preceding paper in this issue
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Part 1: Smith, A. B., III: Condon, S. M.; McCauley, J. A.; Leahy, J. W.; Leazer, J. L., Jr.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1997, 119, 0000 (preceding paper in this issue).
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McCauley, J.A.3
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(c) Baker, H.; Sidorowicz, A.; Sehgal, S. N.; Vézina, C. Ibid. 1978, 31, 539.
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(d) Singh, K.; Sun, S.; Vézina, C. Ibid. 1979, 32, 630.
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(f) McAlpine, J. B.; Swanson, S. J.; Jackson, M.; Whittern, D. N. J. Antibiot. 1991, 44, 688.
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McAlpine, J.B.1
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8
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24844437863
-
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correction
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(g) McAlpine, J. B.; Swanson, S. J.; Jackson, M.; Whittern, D. N. Ibid. 1991, 44, C-3 (correction).
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McAlpine, J.B.1
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(a) Sehgal, S. N.; Baker, H.; Eng, C.; Singh, K.; Vézina, C. J. Antibiot. 1983, 36, 351.
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(b) Findlay, J. A.; Liu, J. S.; Burnell, D. J.; Nakashima, T. T. Can. J. Chem. 1982, 60, 2046.
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14
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0010616713
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5 elegantly extended this methodology by using a Stille-type "stitching-cyclization" to install the C(19,20) vinyl unit and close the macrocycle in 28% yield.
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(a) Nicolaou, K. C.; Piscopio, A. D.; Bertinato, P.; Chakraborty, T. K.; Minowa, N.; Koide, K. Chem. Eur. J. 1995, 1, 318.
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(b) Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419.
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Condon, S. M. Ph.D. Thesis, University of Pennsylvania, 1995.
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Condon, S.M.1
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19
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0029011702
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Preliminary communication: Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1995, 117, 5407.
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Smith III, A.B.1
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Maleczka Jr., R.E.6
-
20
-
-
2742542553
-
-
The intramolecular Stille coupling remains an effective protocol for natural product synthesis. See for example: (a) Pattenden, G.; Thom, S. M. Synlett 1993, 215. (b) Barrett, A. G. M.; Boys, M. L.; Boehm, T. L. J. Org. Chem. 1996, 61, 685.
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Synlett
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Pattenden, G.1
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21
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0030043960
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The intramolecular Stille coupling remains an effective protocol for natural product synthesis. See for example: (a) Pattenden, G.; Thom, S. M. Synlett 1993, 215. (b) Barrett, A. G. M.; Boys, M. L.; Boehm, T. L. J. Org. Chem. 1996, 61, 685.
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Barrett, A.G.M.1
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Preliminary communications: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leahy, J. W.; Leazer, J. L., Jr.; Maleczka, R. E., Jr. Tetrahedron Lett. 1994, 35, 4907. (b) Smith, A. B., III; Maleczka, R. E., Jr.; Leazer, J. L., Jr.; Leahy, J. W.; McCauley, J. A.; Condon, S. M. Ibid. 1994, 35, 4911.
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23
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0028343368
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Preliminary communications: (a) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leahy, J. W.; Leazer, J. L., Jr.; Maleczka, R. E., Jr. Tetrahedron Lett. 1994, 35, 4907. (b) Smith, A. B., III; Maleczka, R. E., Jr.; Leazer, J. L., Jr.; Leahy, J. W.; McCauley, J. A.; Condon, S. M. Ibid. 1994, 35, 4911.
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0009149212
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The (-)-antipode of 11, obtained by resolution, was required for the latrunculins: (a) Zibuck, R.; Liverton, N. J.; Smith, A. B., III J. Am. Chem. Soc. 1986, 108, 2451. (b) Smith, A. B., III; Leahy, J. W.; Noda, I.; Remiszewski, S. W.; Liverton, N. J.; Zibuck, R. Ibid. 1992, 114, 2995.
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Maleczka, R. E., Jr.; Condon, S. M. (University of Pennsylvania). These results will be described elsewhere.
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70
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1842283407
-
-
note
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2. (Equation Presented)
-
-
-
-
71
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0025767167
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Limited success was achieved with bis(tributyltin) oxide. See: Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. Tetrahedron Lett. 1991, 34, 4239.
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0000044010
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McMurry, J. Org. React. 1976, 24, 187. The concentration of 68 was 0.017 M. At higher concentrations, or when the C(10) hemiketal hydroxyl was protected as a TMS ether, rearrangement product 70 was produced as a partially separable 1:1 mixture of isomers. A plausible sequence leading to 70 involves cleavage of both the methyl ester and TES (or TMS) ether, benzilic acid rearrangement, acyl migration, protonation, and decarboxylation. (Equation Presented)
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McMurry, J.1
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DMAP·HCl suppressed formation of the N-acylurea derived from 5. See: Boden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394.
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(b) Steffan, R. J.; Kearney, R. M.; Hu, D. C.; Failli, A. A.; Skotnicki, J. S.; Schiksnis, R. A.; Mattes, J. F.; Chan, K. W.; Caufield, C. E. Ibid. 1993, 34, 3699.
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Steffan, R.J.1
Kearney, R.M.2
Hu, D.C.3
Failli, A.A.4
Skotnicki, J.S.5
Schiksnis, R.A.6
Mattes, J.F.7
Chan, K.W.8
Caufield, C.E.9
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McCauley, J. A. Ph.D. Thesis, University of Pennsylvania, 1996.
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(1996)
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McCauley, J.A.1
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Farina, V.; Baker, S. R.; Benigni, D.; Sapino, C, Jr. Tetrahedron Lett. 1988, 29, 5739.
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(1988)
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Farina, V.1
Baker, S.R.2
Benigni, D.3
Sapino Jr., C.4
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79
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1842359318
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note
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13C. Optical rotations were measured with a Perkin-Elmer Model 241 polarimeter. High-resolution mass spectra were obtained at the University of Pennsylvania Mass Spectrometry Service Center with either a VG Micromass 70/70H or VG ZAB-E spectrometer. Microanalyses were performed by Robertson Laboratories. Madison, NJ. Single-crystal X-ray structure determinations were performed at the University of Pennsylvania with an Enraf Nonius CAD-4 automated diffractometer.
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