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Volumn , Issue 6, 2007, Pages 983-985

A route to the tetrahydrofuran segment of amphidinolides X and Y, and its quaternary-carbon epimer

Author keywords

Amphidinolides; Cyclization; Palladium; Stereoselective synthesis

Indexed keywords

4,5 EPOXY 2 ALKENOIC ACID; ALKENE DERIVATIVE; AMPHIDINOLIDE X; AMPHIDINOLIDE Y; ANTINEOPLASTIC AGENT; PALLADIUM; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

EID: 34247172518     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-973867     Document Type: Article
Times cited : (16)

References (33)
  • 4
    • 30744437649 scopus 로고    scopus 로고
    • For a review on the synthesis of macrodiolide natural products, see
    • For a review on the synthesis of macrodiolide natural products, see: Kang, E. J.; Lee, E. Chem. Rev. 2005, 105, 4348.
    • (2005) Chem. Rev , vol.105 , pp. 4348
    • Kang, E.J.1    Lee, E.2
  • 10
    • 0000560517 scopus 로고    scopus 로고
    • Nicolaou and co-workers pioneered in the study of regioselective hydroxy epoxide openings controlled by a double bond. See: (a) Nicolaou, K. C, Prasad, C. V. C, Somers, P. K, Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330
    • Nicolaou and co-workers pioneered in the study of regioselective hydroxy epoxide openings controlled by a double bond. See: (a) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
  • 14
    • 0034706358 scopus 로고    scopus 로고
    • For recent examples of the use of this methodology in synthesis, see: a
    • For recent examples of the use of this methodology in synthesis, see: (a) Noguchi, Y.; Yamada, T.; Uchiro, H.; Kobayashi, S. Tetrahedron Lett. 2000, 41, 7499.
    • (2000) Tetrahedron Lett , vol.41 , pp. 7499
    • Noguchi, Y.1    Yamada, T.2    Uchiro, H.3    Kobayashi, S.4
  • 18
    • 34247112138 scopus 로고    scopus 로고
    • 2: C, 64.58; H, 10.84; O, 24.58. Found: C, 64.53; H, 10.77; O, 24.21.
    • 2: C, 64.58; H, 10.84; O, 24.58. Found: C, 64.53; H, 10.77; O, 24.21.
  • 19
    • 34247146643 scopus 로고    scopus 로고
    • 3.
    • 3.
  • 21
    • 34247122107 scopus 로고    scopus 로고
    • 3: C, 66.64; H, 9.15; O, 24.24. Found: C, 66.60; H, 9.38; O, 24.01.
    • 3: C, 66.64; H, 9.15; O, 24.24. Found: C, 66.60; H, 9.38; O, 24.01.
  • 22
    • 34247173784 scopus 로고    scopus 로고
    • A small amount of its corresponding Z-isomer was also isolated (5%).
    • A small amount of its corresponding Z-isomer was also isolated (5%).
  • 23
    • 34247100473 scopus 로고    scopus 로고
    • 3: C, 65.97; H, 10.07; O, 23.97. Found: C, 65.72; H, 10.22; O, 24.05.
    • 3: C, 65.97; H, 10.07; O, 23.97. Found: C, 65.72; H, 10.22; O, 24.05.
  • 25
    • 34247131550 scopus 로고    scopus 로고
    • Low diastereoselectivity was observed when the epoxidation was conducted with MCPBA (20% de).
    • Low diastereoselectivity was observed when the epoxidation was conducted with MCPBA (20% de).
  • 26
    • 0026761964 scopus 로고    scopus 로고
    • For examples of the influence of alcohol functions on the diastereoselectivity of the Sharpless epoxidation, see: (a) Takano, S, Setoh, M, Takahashi, M, Ogasawara, K. Tetrahedron Lett. 1992, 33, 5365
    • For examples of the influence of alcohol functions on the diastereoselectivity of the Sharpless epoxidation, see: (a) Takano, S.; Setoh, M.; Takahashi, M.; Ogasawara, K. Tetrahedron Lett. 1992, 33, 5365.
  • 30
    • 34247093553 scopus 로고    scopus 로고
    • Analytical data for 3: oil; [α]D20 -20.1 (c, 1.2, CHCl3, 1H NMR (300 MHz, CDCl 3, δ, 0.90 (t, J, 7.0 Hz, 3 H, 1.32 (s, 3 H, 1.20-1.50 (m, 4H, 1.71 (dd, J, 6.4, 12.8 Hz, 1 H, 2.16 (dd, J, 7.4, 12.8 Hz, 1 H, 2.36 (br s, 1 H, 4.02 (q, J, 6.4 Hz, 1 H, 4.13 (t, J, 6.4 Hz, 1 H, 5.18 (dd, J, 0.9, 10.3 Hz, 1 H, 5.34 (dt, J, 1.3, 17.1 Hz, 1 H, 5.83 (ddd, J, 6.7, 10.3, 17.1 Hz, 1 H, 13C NMR (75 MHz, CDCl3, δ, 14.6, 17.8, 27.2, 45.1 (2 x C, 76.8, 82.6, 85.3, 117.1, 137.2. Anal. Calcd for C10H 18O2: C, 70.55; H, 10.66; O, 18.8. Found: C, 70.35; H, 10.82; O, 18.82. Analytical data for 11: oil; [α]D 20 -16.3 (c, 1, CHCl3, 1H NMR (300 MHz, CDCl3, δ, 0.92 (t, J, 7.0 Hz, 3 H, 1.21 s, 3 H
    • 2: C, 70.55; H, 10.66; O, 18.8. Found: C, 70.77; H, 10.52; O, 18.69. (a) Brown, H. C.; Cope, O. J. J. Am. Chem. Soc. 1964, 86, 1801.
  • 32
    • 34247109326 scopus 로고    scopus 로고
    • 3, >96% ee).
    • 3, >96% ee).
  • 33
    • 34247104355 scopus 로고    scopus 로고
    • 3, 83% ee).
    • 3, 83% ee).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.