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

Abstract

A one-pot synthesis of the title compounds is achieved via highly facile Diels–Alder reactions of 2-methoxyfuran with masked o-benzoquinones.

References

1. G. R. Pettit, G. M. Grag and R. H. Ode, Biosynthetic Products for Cancer Therapy, Plenum, New York, 1977–1979, vol. I-III.
2. P. A. Grieco, Synthesis, 1975, 67; H. M. R. Hoffman and J. Rabe, Angew. Chem., Int. Ed. Engl., 1985, 24, 94; N. Petragnani, H. M. C. Ferraz and G. Silva, Synthesis, 1986, 157.
3. I. Collins, Contemp. Org. Synth., 1997, 4, 281 and 1996, 3, 295; C. H. Heathcock, S. L. Graham, M. C. Pirrung, F. Plavac and C. T. White, in The Total Synthesis of Natural Products, ed. J. ApSimon, Wiley-Interscience, New York, 1982, vol. 5; G. V. Boyd, in The Chemistry of Acid Derivatives, The Chemistry of Functional Groups, ed. S. Patai, Wiley, Chichester, 1979, vol. 1, p. 491 and 1992, vol. 2, p 597; J. F. Wolfe and M. A. Ogliaruso, in The Chemistry of Acid Derivatives, The Chemistry of Functional Groups, ed. S. Patai, Wiley, Chichester, 1979, vol. 1, p. 1063 and refs. cited therein.
4. M. A. Brimble and R. J. Elliot, Tetrahedron, 1997, 53, 7715; C. Camiletti, L. Poletti and C. Trombini, Tetrahedron: Asymmetry, 1996, 7, 1059 and refs. cited therein.
5. C. Alexandre, C. Bertho, B. Tabti and F. Rouessac, Tetrahedron, 1991, 47, 5481; S. D. Burke, D. R. Magnin, J. A. Oplinger, J. P. Baker and A. Abdelmagid, Tetrahedron Lett., 1984, 25, 19; D. Craig, Chem. Soc. Rev., 1987, 16, 187 and refs. cited therein.
6. G. Andersson and P. Berntsson, Acta Chem. Scand., Ser. B, 1975, 29, 948.
7. 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.
8. For some other recent applications of MOBs, see: R. S. Coleman and E. B. Grant, J. Am. Chem. Soc., 1995, 117, 10 889; K. S. Feldman and S. M. Ensel, J. Am. Chem. Soc., 1994, 116, 3357; A. S. Mitchell and R. A. Russell, Tetrahedron Lett., 1993, 34, 545; M. G. Banwell and M. P. Collis, J. Chem. Soc., Chem. Commun., 1991, 1343 and refs. cited therein.
9. C. O. Kappe, S. S. Murphree and A. Padwa, Tetrahedron, 1997, 42, 14 179.
10. E. Wenkert, P. D. R. Moeller and S. R. Piettre, J. Am. Chem. Soc., 1988, 110, 7188; M. E. Jung, L. J. Street and Y. Usui, J. Am. Chem. Soc., 1986, 108, 6810; M. S. Raasch, J. Org. Chem., 1980, 45, 867.
11. C.-H. Chen, P. D. Rao and C.-C. Liao, J. Am. Chem. Soc., 1998, 120, 13254.
12. Method A: General procedure for 2-methoxyphenols2d-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-methoxyphenols2a-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.
13. I. Flemming, Frontier Orbitals and Organic Chemical Reactions, Wiley, Chichester, 1978.
14. S. Sugiyama, T. Tsuda and A. Mori, Chem. Lett., 1986, 1315; S. Sugiyama, T. Tsuda, A. Mori, H. Takeshita and M. Kodama, Bull. Chem. Soc. Jpn., 1987, 60, 3633.
15. G. Casiraghi and G. Rassu, Synthesis, 1995, 607; K. Oda and M. Machida, J. Chem. Soc., Chem. Commun., 1994, 1477.