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For syntheses of o-iodophenols, see: (a) Edgar, K. J.; Falling, S. N. J. Org. Chem. 1990, 55, 5287.
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45
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42049084632
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2O at r.t.
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2O at r.t.
-
-
-
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47
-
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42049105792
-
-
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
-
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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.
-
-
-
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49
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42049122140
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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
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+: 315.1380; found: 315.1378.
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50
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28844489157
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