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Volumn , Issue 3, 2007, Pages 391-394

Synthesis of a malimide analogue of the telomerase inhibitor UCS1025A using a dianionic aldol strategy

Author keywords

Aldol reactions; Diels Alder reactions; Imides; Natural products; Total synthesis

Indexed keywords

DRUG ANALOG; TELOMERASE INHIBITOR; UCS 1025A; UNCLASSIFIED DRUG;

EID: 33847349318     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-968000     Document Type: Article
Times cited : (37)

References (31)
  • 7
    • 0035857396 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 10
    • 0037419451 scopus 로고    scopus 로고
    • Dictyodendrins: (d) Warabi, K.; Matsunaga, S.; van Soest, R. W. M.; Fusetani, N. J. Org. Chem. 2003, 68, 2765.
    • Dictyodendrins: (d) Warabi, K.; Matsunaga, S.; van Soest, R. W. M.; Fusetani, N. J. Org. Chem. 2003, 68, 2765.
  • 12
    • 25444504553 scopus 로고    scopus 로고
    • 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.
    • (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.
  • 14
    • 33847338752 scopus 로고    scopus 로고
    • Dvornikovs, V.; Hoye, T. R. Abstracts of Papers, 229th National Meeting of the American Chemical Society, San Diego CA, March 13-17, 2005; American Chemical Society: Washington D.C., 2005, ORGN 665.
    • (b) Dvornikovs, V.; Hoye, T. R. Abstracts of Papers, 229th National Meeting of the American Chemical Society, San Diego CA, March 13-17, 2005; American Chemical Society: Washington D.C., 2005, ORGN 665.
  • 15
    • 33847347927 scopus 로고    scopus 로고
    • Christmann, M. Abstracts of Papers, 229th National Meeting of the American Chemical Society, San Diego CA, March 13-17, 2005; American Chemical Society: Washington D.C., 2005, ORGN 378.
    • (c) Christmann, M. Abstracts of Papers, 229th National Meeting of the American Chemical Society, San Diego CA, March 13-17, 2005; American Chemical Society: Washington D.C., 2005, ORGN 378.
  • 22
    • 33847411346 scopus 로고    scopus 로고
    • 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
    • 2O, 1:1 → 1:3) gave 8a and 8b as a mixture of diastereomers in 31% and 25% yields, respectively.
  • 23
    • 33847340511 scopus 로고    scopus 로고
    • 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
    • 4: C, 68.12; H, 7.30; N, 4.41. Found: C, 67.84; H, 7.76; N, 4.26.
  • 31
    • 33847362153 scopus 로고    scopus 로고
    • 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
    • 4Si: 438.21006; found: 438.21006.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.