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Volumn , Issue 6, 2008, Pages 940-944

Gold-catalyzed double intramolecular alkyne hydroalkoxylation: Synthesis of the bisbenzannelated spiroketal core of rubromycins

Author keywords

Alkyne hydroalkoxylation; Coupling; Gold catalysis; Rubromycin; Spiroketal

Indexed keywords

ALKYNE; ANTIBIOTIC AGENT; GOLD; RUBROMYCIN; SPIRO COMPOUND; UNCLASSIFIED DRUG;

EID: 42049119847     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1042910     Document Type: Article
Times cited : (78)

References (51)
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    • For a synthesis of bisbenzannelated 6,6-spiroketals, see
    • (b) For a synthesis of bisbenzannelated 6,6-spiroketals, see: Zhou, G.; Zheng, D.; Da, S.; Xie, Z.; Li, Y. Tetrahedron Lett. 2006, 47, 3349.
    • (2006) Tetrahedron Lett , vol.47 , pp. 3349
    • Zhou, G.1    Zheng, D.2    Da, S.3    Xie, Z.4    Li, Y.5
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    • For syntheses of the isocoumarin subunit, see: a
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    • (2000) Tetrahedron Lett , vol.41 , pp. 29
    • Thrash, T.P.1    Welton, T.D.2    Behar, V.3
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    • For syntheses of the naphthalene subunit of rubromycin and related structures, see
    • (d) For syntheses of the naphthalene subunit of rubromycin and related structures, see: Brasholz, M.; Luan, X.; Reissig, H.-U. Synthesis 2005, 3571.
    • (2005) Synthesis , pp. 3571
    • Brasholz, M.1    Luan, X.2    Reissig, H.-U.3
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    • For a review of gold-catalyzed reactions, see: a
    • For a review of gold-catalyzed reactions, see: (a) Hashmi, A. S. K. Gold Bull. 2004, 37, 51.
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    • Hashmi, A.S.K.1
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    • For a synthesis of alkyne 5, see: Trost, B. M.; Shen, H. C.; Li, D.; Surivet, J. P.; Sylvain, C. J. Am. Chem. Soc. 2004, 126, 11966.
    • For a synthesis of alkyne 5, see: Trost, B. M.; Shen, H. C.; Li, D.; Surivet, J. P.; Sylvain, C. J. Am. Chem. Soc. 2004, 126, 11966.
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    • For syntheses of o-iodophenols, see: (a) Edgar, K. J.; Falling, S. N. J. Org. Chem. 1990, 55, 5287.
    • For syntheses of o-iodophenols, see: (a) Edgar, K. J.; Falling, S. N. J. Org. Chem. 1990, 55, 5287.
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    • 2O at r.t.
    • 2O at r.t.
  • 47
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    • 2 at r.t. for 2 d provided the aromatic spiroketal 7a in 61% yield.
    • 2 at r.t. for 2 d provided the aromatic spiroketal 7a in 61% yield.
  • 48
    • 42049086314 scopus 로고    scopus 로고
    • 2 (4 mL). After the reaction mixture had been stirred at r.t. for 2 d, the solvent was removed and the residue purified by flash chromatography on silica gel (hexane-EtOAc, 8:1 v/v) to give the bisspiroketal 7a (30.0 mg, 62%) as a white solid.
    • 2 (4 mL). After the reaction mixture had been stirred at r.t. for 2 d, the solvent was removed and the residue purified by flash chromatography on silica gel (hexane-EtOAc, 8:1 v/v) to give the bisspiroketal 7a (30.0 mg, 62%) as a white solid.
  • 49
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    • Spectral Data for Selected Compounds (Table 2) Compound 7b: white solid; mp 115-117°C 1H NMR (300 MHz, CDCl3, δ, 7.13-7.07 (m, 2 H, 7.04 (s, 1 H, 6.95-6.88 (m, 2 H, 6.78 (d, J, 8.4 Hz, 1 H, 6.68 (d, J, 8.1 Hz, 1 H, 3.40 (d, J, 16.5 Hz, 1 H, 3.30-3.18 (m, 2 H, 2.81 (ddd, J, 16.5, 6.0, 24 Hz, 1 H, 2.35-2.29 (m, 4 H, 2.17 (td, J, 12.6, 6.3 Hz, 1 H, 13C NMR (75 MHz, CDCl3, δ, 155.8, 152.3, 130.4, 129.1, 128.4, 127.4, 125.4, 125.3, 121.4, 121.1, 117.1, 109.4, 109.0, 41.9, 30.4, 21.9, 20.8. IR: ν, 3020 (CH, arom, 2925 (CH, 1584, 1489 (ArC=C, 1080, 1045 (CO) cm -1. ESI-HRMS: m/z calcd for C17H16O 2Na [M, Na, 275.1043; found: 275.1046. Compound 7c: pale yellow solid; mp 173-175°C 1H NMR (300 MHz, CDCl3, δ, 7.26 (s, 1 H, 7.19-7.08 (m, 3 H, 6.91 td, J
    • +: 315.1380; found: 315.1378.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.