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7
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0035857396
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Telomestatin: (a) Shinya, K.; Wierzba, K.; Matsuo, K.-I.; Ohtani, T.; Yamada, Y.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Am. Chem. Soc. 2001, 123, 1262.
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Telomestatin: (a) Shinya, K.; Wierzba, K.; Matsuo, K.-I.; Ohtani, T.; Yamada, Y.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Am. Chem. Soc. 2001, 123, 1262.
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8
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21644460419
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Dictyodendrins: (d) Warabi, K.; Matsunaga, S.; van Soest, R. W. M.; Fusetani, N. J. Org. Chem. 2003, 68, 2765.
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11
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Fürstner, A.1
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Axinelloside: Warabi, K.; Hamada, T.; Nakao, Y.; Matsunaga, S.; Hirota, H.; van Soest, R. W. M.; Fusetani, N. J. Am. Chem. Soc. 2005, 127, 13262.
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(f) Axinelloside: Warabi, K.; Hamada, T.; Nakao, Y.; Matsunaga, S.; Hirota, H.; van Soest, R. W. M.; Fusetani, N. J. Am. Chem. Soc. 2005, 127, 13262.
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33847347927
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22
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33847411346
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Typical Procedure: THF (4.5 mL) was cooled to 0°C and NaHMDS (1.02 mL, 2.0 M in THF, 2.05 mmol) was added. To this solution the benzyl-protected (S)-3-hydroxypyrrolidine-2,5-dione (0.20 g, 0.97 mmol) in THF (3.2 mL) was added dropwise and after complete addition the solution was stirred at 0°C for an additional 5 min to give a yellowish suspension. The reaction mixture was cooled to -78°C, cyclohexyl carbaldehyde (0.12 mL, 0.97 mmol) in THF (2.2 mL) was added dropwise and the resulting mixture was stirred at -78°C for 1 h. The reaction was quenched with sat. NH4Cl (5 mL) and diluted with Et2O (30 mL) and CH2Cl2 (10 mL, The organic layer was washed with sat. NH4Cl (2 x 5 mL, dried (Na2SO4) and concentrated. Purification by column chromatography (SiO2; n-pentane-Et2O, 1:1 → 1:3) gave 8a and 8b as a mixture of diastereomers in 31% and
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2O, 1:1 → 1:3) gave 8a and 8b as a mixture of diastereomers in 31% and 25% yields, respectively.
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23
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33847340511
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Compound 8a: mp 135-137°C; [α]25D -9.8 (c, 1.01, acetone, Rf 0.19 (n-pentane- Et2O, 1:1, 1H NMR (400 MHz, CDCl3, δ, 7.18-7.27 (m, 5 H, 4.66 (d, J, 5.2 Hz, 1 H, 4.61 (d, J, 14.6 Hz, 1 H, 4.57 (d, J, 14.3 Hz, 1 H, 3.96 (dd, J, 2.2, 9.1 Hz, 1 H, 2.93 (dd, J, 2.3, 5.1 Hz, 1 H, 2.20 (br s, 1.95 (d, J, 12.4 Hz, 1 H, 1.58-1.76 (m, 4 H, 1.44-1.55 (m, 1 H, 1.02-1.26 (m, 3 H, 0.84-0.96 (m, 2 H, 13C NMR (100 MHz, CDCl3, δ, 177.8, 176.2, 135.2, 128.7 (2 x C, 128.3 (2 x C, 127.9, 73.2, 67.3, 51.8, 42.7, 41.3, 29.3, 28.8, 26.3, 25.9, 25.8. IR (KBr, 3462, 2924, 2851, 1696, 1438, 1407, 1356, 1168, 697 cm-1. MS (EI, m/z, 318 (26, 317 (83, M, 299 (23, 234 (77, 205 (74, 204 (36, 127 (17, 106 (26, 96 (25, 95 (31, 92 (23, 91 (100, 73 (26, 71 18, 56
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4: C, 68.12; H, 7.30; N, 4.41. Found: C, 67.84; H, 7.76; N, 4.26.
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24
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0037453621
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Edmonds, D. J.; Muir, K. W.; Procter, D. J. J. Org. Chem. 2002, 68, 3190.
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Edmonds, D.J.1
Muir, K.W.2
Procter, D.J.3
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25
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33847798412
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Huang, S. L.; Omura, K.; Swern, D. J. Org. Chem. 1976, 41, 3329.
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Huang, S.L.1
Omura, K.2
Swern, D.3
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29
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23944490138
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Wilson, R. M.; Jen, W. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 11616.
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J. Am. Chem. Soc
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Wilson, R.M.1
Jen, W.S.2
MacMillan, D.W.C.3
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30
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0037162657
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Hagiwara, H.; Kobayashi, K.; Miya, S. T.; Suzuki, T.; Ando, M.; Okamoto, T.; Kobayashi, M.; Yamamoto, I.; Ohtsubo, S.; Kato, M.; Uda, H. J. Org. Chem. 2002, 67, 5969.
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J. Org. Chem
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Hagiwara, H.1
Kobayashi, K.2
Miya, S.T.3
Suzuki, T.4
Ando, M.5
Okamoto, T.6
Kobayashi, M.7
Yamamoto, I.8
Ohtsubo, S.9
Kato, M.10
Uda, H.11
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31
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33847362153
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Compound 2: colorless oil; Rf 0.38 (pentane-EtOAc, 10:1, 1H NMR (300 MHz, CDCl3, δ, 11.51 (s, 7.18 (m, 5.38 (m, 5.22 (d, J, 9.9 Hz, 4.76 (s, 4.68 (d, J, 4.2 Hz, 4.54 (d, J, 14.3 Hz, 4.53 (d, J, 14.3 Hz, 4.44 (d, J, 14.1 Hz, 4.42 (d, J, 14.1 Hz, 3.65 (d, J, 4.2 Hz, 2.95 (dd, J, 5.4, 11.1 Hz, 2.62 (m, 2.18 (d, J, 8.2 Hz, 1.33-1.68 (m, 1.08-1.22 (m, 0.90 (d, J, 6.7 Hz, Me, 0.72 (s, 0.71 (s, 0.08 (s, 0.03 (s, 0.01 (s, 0.00 (s, 13C NMR (75 MHz, CDCl3, δ, 204.8, 176.8, 174.7, 174.2, 173.5, 170.1, 135.6, 134.9, 131.4, 130.8, 130.4 (2 x C, 128.7 (2 x C, 128.6 (2 x C, 128.5 (4 x C, 127.9, 127.8, 101.7, 70.1, 68.1, 64.5, 57.4, 46.9, 42.9, 42.5, 42.3, 41.5, 37.3, 36.2, 34.6, 32.8 (2 x C, 30.5, 30.2, 29.8, 26.5, 26.4, 26.3, 26.2, 25.6 (3 x C, 25.4 (3 x C, 18.1, 17.9, 17.5, 3.9, 4.4, 4.9, 5.4. IR CHCl
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4Si: 438.21006; found: 438.21006.
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