메뉴 건너뛰기




Volumn 65, Issue 20, 2000, Pages 6703-6707

Stereoselective synthesis of 7,11-guaien-8,12-olides from santonin. Synthesis of podoandin and (+)-zedolactone A

Author keywords

[No Author keywords available]

Indexed keywords

7,11 GUAIEN 8,12 OLIDE DERIVATIVE; PODOANDIN; SANTONIN; UNCLASSIFIED DRUG; ZEDOLACTONE A;

EID: 0034613314     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000927h     Document Type: Article
Times cited : (42)

References (63)
  • 3
    • 0000137613 scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1985) Nat. Prod. Rep. , vol.2 , pp. 147
    • Fraga, B.M.1
  • 4
    • 57749168980 scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1986) Nat. Prod. Rep. , vol.3 , pp. 273
  • 5
    • 0023429002 scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1987) Nat. Prod. Rep. , vol.4 , pp. 473
  • 6
    • 0000095830 scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1988) Nat. Prod. Rep. , vol.5 , pp. 497
  • 7
    • 0011234134 scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1990) Nat. Prod. Rep. , vol.7 , pp. 61
  • 8
    • 0343608470 scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1990) Nat. Prod. Rep. , vol.7 , pp. 515
  • 9
    • 0347386345 scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1993) Nat. Prod. Rep. , vol.9 , pp. 217
  • 10
    • 0013603594 scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1992) Nat. Prod. Rep. , vol.9 , pp. 557
  • 11
    • 0000569057 scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1993) Nat. Prod. Rep. , vol.10 , pp. 397
  • 12
    • 0011250707 scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1994) Nat. Prod. Rep. , vol.11 , pp. 533
  • 13
    • 0029141020 scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1995) Nat. Prod. Rep. , vol.12 , pp. 303
  • 14
    • 0029987404 scopus 로고    scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1996) Nat. Prod. Rep. , vol.13 , pp. 307
  • 15
    • 0030939920 scopus 로고    scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1997) Nat. Prod. Rep. , vol.14 , pp. 145
  • 16
    • 0039373838 scopus 로고    scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1998) Nat. Prod. Rep. , vol.15 , pp. 73
  • 17
    • 0003587578 scopus 로고    scopus 로고
    • (c) Fraga, B. M. Nat. Prod. Rep. 1985, 2, 147; 1986, 3, 273; 1987, 4, 473; 1988, 5, 497; 1990, 7, 61; 1990, 7, 515; 1993, 9, 217; 1992, 9, 557; 1993, 10, 397; 1994, 11, 533; 1995, 12, 303; 1996, 13, 307; 1997, 14, 145; 1998, 15, 73; 1999, 16, 21.
    • (1999) Nat. Prod. Rep. , vol.16 , pp. 21
  • 52
    • 0342403160 scopus 로고    scopus 로고
    • note
    • 1H NMR (300 MHz) δ 7.02 (1H, s), 5.35 (1H, br s), 2.98 (1H, d, J = 16.5), 2.91 (1H, d, J = 16.5), 1.90 (3H, d, J = 1.5), 1.66 (3H, br s), 1.29 (3H, s).
  • 55
    • 0343272745 scopus 로고    scopus 로고
    • note
    • 1H NMR (300 MHz) δ 5.39 (1H, br s), 4.95 (1H, br dd, J = 5.4, 6.5), 2.92 (1H, dd, J = 3.9, 13.8), 2.70-2.60 (1H, m), 2.49 (1H, dd, J = 8.4, 15.6), 2.42 (1H, dd, J = 6.5, 15.2), 2.30-2.22 (2H, m), 2.07 (1H, dd, J = 7.2, 13.8), 2.00 (1H, br dd, J = 5.4, 15.2), 1.83 (3H, d, J = 2.1), 1.74 (3H, d, J = 1.8), 1.27 (3H, s).
  • 61
    • 0342837873 scopus 로고    scopus 로고
    • For a general description of the experimental procedures employed in this research, see ref 10
    • For a general description of the experimental procedures employed in this research, see ref 10.
  • 62
    • 0000433635 scopus 로고
    • Wiley & Sons: New York; Collect
    • (a) Mozingo, R. Organic Syntheses; Wiley & Sons: New York, 1955; Collect. Vol III, p 181.
    • (1955) Organic Syntheses , vol.3 , pp. 181
    • Mozingo, R.1
  • 63
    • 0343708299 scopus 로고    scopus 로고
    • W-2 Raney Ni was deactivated by heating the ethanolic suspension at 60°C for 3-4 days
    • (b) W-2 Raney Ni was deactivated by heating the ethanolic suspension at 60°C for 3-4 days.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.