One-pot stereoselective synthesis of tricyclic γ-lactones from 2-methoxyfuran and 2-methoxyphenols

Chemical Communications

Volumn , Issue 8, 1999, Pages 713-714

  Rao, Polisetti Dharma ^a   Chen, Chien Hsing ^a   Liao, Chun Chen ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN; GAMMA LACTONE DERIVATIVE; GUAIACOL;

ARTICLE; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033590944     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901267b     Document Type: Article

References (38)

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18. For reactions of MOBs as dienes, see: D.-S. Hsu, P. D. Rao and C.-C. Liao, Chem. Commun., 1998, 1795; P. D. Rao, C.-H. Chen and C.-C. Liao, Chem. Commun., 1998, 155; P.-Y. Hsu, Y.-C. Lee and C.-C. Liao, Tetrahedron Lett., 1998, 39, 659; W.-C. Liu and C.-C. Liao, Synlett, 1998, 912; P.-Y. Hsiu and C.-C. Liao, Chem. Commun., 1997, 1085; R. Carlini, K. Higgs, C. Older and S. Randhawa, J. Org. Chem., 1997, 62, 2330; C.-S. Chu, C.-C. Liao and P. D. Rao, Chem. Commun., 1996, 1537 and refs. cited therein.
19. For reactions of MOBs as dienes, see: D.-S. Hsu, P. D. Rao and C.-C. Liao, Chem. Commun., 1998, 1795; P. D. Rao, C.-H. Chen and C.-C. Liao, Chem. Commun., 1998, 155; P.-Y. Hsu, Y.-C. Lee and C.-C. Liao, Tetrahedron Lett., 1998, 39, 659; W.-C. Liu and C.-C. Liao, Synlett, 1998, 912; P.-Y. Hsiu and C.-C. Liao, Chem. Commun., 1997, 1085; R. Carlini, K. Higgs, C. Older and S. Randhawa, J. Org. Chem., 1997, 62, 2330; C.-S. Chu, C.-C. Liao and P. D. Rao, Chem. Commun., 1996, 1537 and refs. cited therein.
20. For reactions of MOBs as dienes, see: D.-S. Hsu, P. D. Rao and C.-C. Liao, Chem. Commun., 1998, 1795; P. D. Rao, C.-H. Chen and C.-C. Liao, Chem. Commun., 1998, 155; P.-Y. Hsu, Y.-C. Lee and C.-C. Liao, Tetrahedron Lett., 1998, 39, 659; W.-C. Liu and C.-C. Liao, Synlett, 1998, 912; P.-Y. Hsiu and C.-C. Liao, Chem. Commun., 1997, 1085; R. Carlini, K. Higgs, C. Older and S. Randhawa, J. Org. Chem., 1997, 62, 2330; C.-S. Chu, C.-C. Liao and P. D. Rao, Chem. Commun., 1996, 1537 and refs. cited therein.
21. For reactions of MOBs as dienes, see: D.-S. Hsu, P. D. Rao and C.-C. Liao, Chem. Commun., 1998, 1795; P. D. Rao, C.-H. Chen and C.-C. Liao, Chem. Commun., 1998, 155; P.-Y. Hsu, Y.-C. Lee and C.-C. Liao, Tetrahedron Lett., 1998, 39, 659; W.-C. Liu and C.-C. Liao, Synlett, 1998, 912; P.-Y. Hsiu and C.-C. Liao, Chem. Commun., 1997, 1085; R. Carlini, K. Higgs, C. Older and S. Randhawa, J. Org. Chem., 1997, 62, 2330; C.-S. Chu, C.-C. Liao and P. D. Rao, Chem. Commun., 1996, 1537 and refs. cited therein.
22. For reactions of MOBs as dienes, see: D.-S. Hsu, P. D. Rao and C.-C. Liao, Chem. Commun., 1998, 1795; P. D. Rao, C.-H. Chen and C.-C. Liao, Chem. Commun., 1998, 155; P.-Y. Hsu, Y.-C. Lee and C.-C. Liao, Tetrahedron Lett., 1998, 39, 659; W.-C. Liu and C.-C. Liao, Synlett, 1998, 912; P.-Y. Hsiu and C.-C. Liao, Chem. Commun., 1997, 1085; R. Carlini, K. Higgs, C. Older and S. Randhawa, J. Org. Chem., 1997, 62, 2330; C.-S. Chu, C.-C. Liao and P. D. Rao, Chem. Commun., 1996, 1537 and refs. cited therein.
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33. Method A: General procedure for 2-methoxyphenols 2d-l: A solution of phenol 2 (1 mM) in MeOH (10 mL) was cooled to 0 °C and DAIB (1.1 mM) was added as solid in one portion. After 10 min of stirring at 0 °C, 2-methoxyfuran (5 mM) was added and the cooling bath was removed. The reaction mixture was stirred at room temperature for 2-4 h (2 h for 2d-f and 4 h for 2g-l) and then MeOH and other volatile materials were removed under reduced pressure. The residue was dissolved in THF and p-TsOH (100 mg) and water (3 drops) were added. The resulting solution was stirred for 4 h at room temperature and the volatiles were then removed under reduced pressure. The residue was purified by column chromatography on silica gel using 40% ethyl acetate in hexanes as eluent to obtain lactone 3 as a colorless solid. Method B: General procedure for 2-methoxyphenols 2a-c: To a mixture of 2-methoxyphenol (1 mM) and 2-methoxyfuran (5 mM) in MeOH (4 mL) was added a solution of DAIB (1.2 mM) in MeOH (6 mL) during a period of time (10 min for 2a and 2c and 80 min for 2b) using a syringe pump at room temperature. After stirring for a further 1 h, MeOH and other volatile materials were removed under reduced pressure and the residue was subjected to hydrolysis as described in method A.
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