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First total synthesis of ocimarin

First total synthesis of ocimarin
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摘要 A facile approach for the first synthesis of ocimarin, naturally occurring coumarins, was developed by employing a cerium (III) chloride heptahydrate-catalyzed Pechmann condensation of phenols and β-keto esters in a solvent-free system as key step, by which ocimarin was achieved by three steps starting from acetylacetic ether and resorcinol with total yield 23.2%. All structures of new compounds were confirmed by IR, ^1H NMR and MS. A facile approach for the first synthesis of ocimarin, naturally occurring coumarins, was developed by employing a cerium (III) chloride heptahydrate-catalyzed Pechmann condensation of phenols and β-keto esters in a solvent-free system as key step, by which ocimarin was achieved by three steps starting from acetylacetic ether and resorcinol with total yield 23.2%. All structures of new compounds were confirmed by IR, ^1H NMR and MS.
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2010年第10期1165-1166,共2页 中国化学快报(英文版)
基金 financially supported by the National Natural Science Foundation of China(Nos. 0562010,20962016) Ministry of National Education(No.203143) Program for New Century Excellent Talents in University
关键词 COUMARINS Ocimarin CeCl3.7H2O Total synthesis Coumarins Ocimarin CeCl3.7H2O Total synthesis
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参考文献7

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  • 7Spectral data of ocimarin:brown,amorphous powder,mp 245-246 ℃; UV (MeOH,bm) λmax 316,275; IR (KBr,cm-1)max 3287,1670,1611,1258,1096; 1H NMR (400 MHz,DMSO-d6):δ 7.60 (d,1H,J = 8.4 Hz,ArH),6.79 (dd,1 H,J = 2.2,8.6 Hz,ArH),6.68 (d,1H,J = 2.4 Hz,ArH),4.69 (S,1H,-OH),3.49 (t,2H,J = 7 Hz,-CH2-CH2-OH),2.71 (t,2H,J = 7 Hz,-CH2-CH2-OH),2.37 (s,3H,-CH3); EIMS m/z[M] +:220 (17),189 (100),84 (99),66 (95),55 (70),43 (97).

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