190
Views
36
CrossRef citations to date
0
Altmetric
Original Articles

OXIDATIVE REARRANGEMENT OF FURYLCARBINOLS TO 6-HYDROXY-2H-PYRAN-3(6H)-ONES, A USEFUL SYNTHON FOR THE PREPARATION OF A VARIETY OF HETEROCYCLIC COMPOUNDS, A REVIEW

, &
Pages 95-118 | Received 29 Nov 1991, Published online: 18 Feb 2009

References

  • Clauson-Kaas , N. 1947 . Kgl. Danske Videnskab. Selskab. Mat.-frs. Medd. , 24 ( No. 6 ) : 18 Chem. Abstr., 42, 1930f (1948)
  • Elming , N. 1960 . Advances Org. Chem. , 2 : 67
  • Lefebvre , Y. Filed in United States for American Home Products on July 29, 1968; granted on December 15, 1970 as U.S. Patent No. 3,547,912, Chem. Abstr, 72, 32133y (1970). For details of experimental data, see ref. 7. b) G. Cavill and coworkers submitted their manuscript for publication May 29, 1959, see ref. 4
  • Cavill , G. W. , Lang , D. G. and Williams , P. J. 1969 . Aust. J. Chem. , 22 : 2145
  • Lefebvre , Y. 1972 . Tetrahedron Lett. , : 133
  • Achmatowicz , O. Jr. , Bukowski , P. , Szechner , B. , Zwierzchowska , Z. and Zamojski , A. 1971 . Tetrahedron , 27 : 1973
  • Laliberte , R. , Medawar , G. and Lefebvre , Y. 1973 . J. Med. Chem. , 16 : 1084
  • Ferland , J. M. , Lefebvre , Y. , Deghenghi , R. and Wiesner , K. 1966 . Tetrahedron Lett. , : 3617 b) K. Wiesner and coworkers, see ref. 13d.
  • Achmatowicz , O. Jr. and Bukowski , P. 1975 . Can. J. Chem. , 13 : 2524 b) O. Achmatowicz, Jr. and G. Grynkiewicz, Rocz. Chem., 50, 719 (1976). Chem. Abstr., 86, 140389j (1977). See also ref. 11a, b and 6. c) O. Achmatowicz, Jr and G. Grynkiewicz, Carbohydr. Research, 54, 193 (1977). d) O. Achmatowicz, Jr. in “Organic Synthesis Today and Tomorrow,” B. M. Trost and C. R. Hutchinson, Eds., Pergamon Press, New York, NY, 1981, p 307. e) A. Zamojski, A. Bamaszek, G. Grynkiewicz, Adv. Carbohydr. Biochem., 40, 1 (1982) and Eferences therein. f) A. Zamojski and G. Grynkiewicz in “The Total Syntheis of Natural Products,” J. ApSimon, Ed. Wiley & Sons, New York, NY, 1984; p. 141. g) P. G. Sammes and D. Thetford, J. Chem. Soc., Perkin Trans. I 111 (1988). h) J. Raczko, A. Golebiowski, J. W. Krajewski, P. Gluzinski and J. Jurczak, Tetrahedron Lett., 31, 3797 (1990). i) B. Szechner, Tetrahedron Lett., 30, 3829 (1987). j) M. P. Georgiadis and E. A. Couladouros, J. Heterocyclic Chem., 28, 1325 (1991). See also Ieference 12f.
  • Holder , N. 1982 . Chem. Rev. , 82 : 287
  • Achmatowicz , O. Jr. , Grynkiewicz , G. and Szechner , B. 1976 . Tetrahedron , 32 : 1051 For some leading references see: b) O. Achmatowicz, Jr. and R. Bielski, Carbohydr. Res., 55, 165 (1977) and references therein. c) O. Achmatowicz, Jr. and M. Burzynska, Polish J. Chem., 53, 265 (1979). Chem. Abstr., 91, 91035h (1979). d) G. Piancatelli, A. Scettri and M. D'Auria, Tetrahedron Lett. 2199 (1977), see also Tetrahedron, 36, 661 (1980). For a general use of PCC, see: Synthesis 245 (1982). e) P. D. Weeks, T. M. Brennan, D. P. Brannegan, D. E. Kuhla, M. L. Elliott, H. A. Watson, B. Wlodecki and R. Breitenbach, J. Org. Chem., 45, 1109 (1980). See also reference therein: S. Torii, H. Tanaka, T. Anoda and Y. Simizu, Chemistry Lett. 495 (1976). f) T. Shono, Y. Matsamuza, K. Tsubata and J. Takata, ibid. 1121 (1981). g) M. P. Georgiadis, E. A. Couladouros, M. G. Polisssiou, S. E. Filippakis, D. Mantzafos and A. Terzis, J. Org. Chem., 47, 3054 (1982). h) T. L. Ho and S. G. Sapp, Synth. Comm., 13, 207 (1983). i) R. Antonioletti, M. D'Auria, A. DeMico, G. Piancatelli and A. Scettri, Tetrahedron, 40, 3805 (1984), and references therein. j) M. P. Georgiadis, E. A. Couladouros, J. Org. Chem., 51, 2725 (1986). k) W. -S. Zou, Z. -H. Lu and 2. -M. Wang, Tetrahedron Lett., 32, 1467 (1991), see also ref. 19a, d, e, 1. l) M. P. Georgiadis, S. A. Haroutounian and C. Apostolopoulos, Synthesis 379 (1991).
  • Georgiadis , M. P. 1976 . J. Med. Chem. , 19 : 34 For some representative examples of 2H-pyran-3(6H)-ones as key intermediates or starting material for the synthesis of medicinally interesting compounds see: See also ref. 11j and ref. 7. b) M. P. Georgiadis, Medicinally Interesting Compounds from 2H-pyran-3(6H)-ones Proceedings of Xth Intemat. Symposium on Med. Chemistry, 1988, Budapest, Trends in Medicinal Chem. Pharmacochemistry Library 12, p. 197 (1989), H. Vander Goot, G. Domany, L. Pallos and H. Timmerman, Eds. c) M. P. Georgiadis, C. D. Apostolopoulos and S. A. Haroutounian, J. Heterocyclic Chem., 28, 599 (1991). d) M. P. Georgiadis, S. A. Haroutounian, E. A. Couladouros, C. D. Apostolopoulos and K. P. Chondros, ibid., 28, 697 (1991). e) M. P. Georgiadis and S. A. Haroutounian, ibid., in press. f) V. Coustantinou-Kokotou, E. A. Couladouros, M. P. Georgiadis, G. C. Kokotos and T. M. Georgiadis, Carbohydr. Res., (1991). in press.
  • For some representative examples of the use of furans as key intermediates in the syntheses of natural products see: Ref. 9 and 14 may be classified also as natural products. b) K. Wiesner, T. Y. R. Tsai, A. Sen, R. Kumar and M. Tsubuki, Helv. Chim. Acta., 66, 2632 (1983). c) T. Kametani, M. Tsubuki, H. Furuyama and T. Honda, Chem. Commun. 375 (1984). d) F. E. Ziegler and R. T. Wester, Tetrahedron Lett., 25, 617 (1984), ibid., 22, 488(1981). e) P. DeShong, S. Ramesh, J. Elango and J. J. Perez, J. Am. Chem. Soc., 107, 5219 (1985). f) P. DeShong, M. T. Lin and J. J. Perez, Tetrahedron Lett., 27, 2091 (1986). g) K. Mori and H. Kisida, Tetrahedron, 42, 5281 (1986). h) S. F. Martin and D. E. Guinn, ibid., 52, 5589 (1987). i) P. DeShong, S. Ramesh, J. Elango and J. J. Perez, ibid., 48, 2117 (1983). j) P. DeShong, D. M. Simpson and M.-T. Lin, Tetrahedron Lett., 30, 2885 (1989). k) T. Honda, Y. Kobayashi and M. Tsubugi ibid., 31, 4891 (1990). l) I. Paterson, M. A. Listerm and G. R. Ryan, ibid., 32, 1749 (1991) and ref. therein. m) P. DeShong, D. A. Simpson, A. Chuljin, S. I. Shimshock, R. E. Waltermire and Y. Class, Fourth Chem Congress of North American #294, August, 1991, New York, NY. n) M. E. Meir and B. Schöffling Tetrahedron Lett., 32, 53 (1991). o) P. G. Sammes and L. J. Street, J. Chem. Soc. Perkin Trans I 1261 (1983). p) S. M. Bromidge, P. G. Sammes and L. J. Street, ibid. 1725 (1985). q) P. G. Sammes, Chem. Comm. 896 (1983). r) P. A. Wender, Y. H. Lee, R. S. Wilhelm and P. D. Williams, J. Am. Chem. Soc., 111, 8954 (1989). s) H. C. Kolb and M. R. Hoffman, Tetrahedron Asymmetry, 1, 237 (1990). t) D. A. Stolze, F. Perron-Sierra, M. J. Heeg and K. F, Albizati, Tetrahedron Lett., 32, 4081 (1991). u) P. Kocienski, F. Yagamare and R. Whitby, J. Chem. Soc., Perkin Trans. 841 (1989)
  • DeShong , P. , Waltermine , R. E. and Ammon , L. 1988 . J. Am. Chem. Soc. , 110 : 1901 b) F. Perron and K. F. Alblzati, Chem. Rev., 89, 1617 (1989). c) F. Perron and K. Albizati, J. Org. Chem., 54, 2044 (1989). d) K. F. Albizati, unpublished results.
  • Shono , T. and Matsumura , Y. 1976 . Tetrahedron Lett. , : 1363
  • Torii , S. , Tanaka , H. , Anod , T. and Simizu , Y. 1976 . Chemistry Lett. , : 495
  • Pikul , S. , Jurczak , J. and Gryzkiewicz , G. 1987 . Bull. Polish Acad. Sci. Chem. , : 35 Chem. Abstr, 109, 128772q (1988).
  • Georgiadis , M. P. and Lefebvre , T. 1983 . Chimika Chronika New Ser. International Ed. , 12 : 45 Chem. Abstr, 99, 194770p (1983). See also C. Apostolopoulos, PhD. Thesis (1991), Agricultural University of Athens, Athens, Greece.
  • Martin , S. F. and Quinn , D. E. 1984 . Tetrahedron Lett. , 25 : 5607 For preparing optically active furylcarbinols, see b) A. Van Oeveren, W. Menge and B. L. Feringa, ibid., 30, 6427 (1989). c) T. Kametani, M. Tsubuki, Y. Tatsuzaki and T. Honda, Heterocycles, 27, 2107 (1988). d) Y. Kobayashi, M. Kusakabe, Y. Kitano and F. Sato, J. Org. Chem., 53, 1586 (1988). e) Y. Kobayashi, M. Kusakabe, Y. Kitano and F. Sato, ibid., 54, 2085 (1989). f) T. Honda, T. Kametani, K. Kanai, Y. Tazuzaki and M. Tsubuki, J. Chem. Soc., Perkin Trans I 1733 (1990) and references therein. g) D. G. Drueckhammer, C. F. Barbas, K. Nozaki, C. -H. Wong, C. Y. Wood and M. A. Ciufolini, J. Org. Chem., 53, 1607 (1988). h) H. Waldman, Tetrahedron Lett., 30, 3057 (1989). For the use of the Sharpless reagent for kinetic resolution, see: i) V. S. Martin, S. S. Woodard, T. Katasuki, Y. Yameda, M. Ikeda. K. B. Sharpless, J. Am. Chem. Soc., 103, 6237 (1981). j) Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, K. B. Sharpless, ibid, 109, 5765(1987).
  • Fraser-Reid , B. , McLean , A. and Usherwood , E. W. 1969 . J. Am. Chem. Soc. , 91 : 5392 b) B. Fraser-Reid, A. McLean, E. W. Usherwood and M. Yunker, Can. J. Chem., 48, 2877 (1970).
  • Hauser , F. M. , Ellenberger , S. F. and Ellenberger , W. P. 1988 . Tetrahedron Lett. , 29 : 4939 b) I. K. Grapsas, E. A. Couladouros and M. P. Georgiadis, Polish J. Chem., 64, 823 (1990). Chem. Abstr., 115, 72036g (1991).
  • Constantinou-Kokotou , V. , Couladouros , E. A. , Georgiadis , M. P. and Kokotos , G. C. 1991 . J. Carbohydr. Chem. , 10 : 749
  • Georgiadis , M. P. 1986 . J. Heterocyclic Chem. , 23 : 605 b) O. Achrnatowicz, Jr. and B. Szechner, Tetrahedron Lett. 1205 (1972).
  • Constantinou-Kokotou , V. , Kokotos , G. and Georgiadis , M. P. 1991 . Ann. , : 151 b) M. P. Georgiadis and E. A. Couladouros, J. Heterocyclic Chem., 27, 1757 (1990), see also ref. 12e and 12f.
  • Zuzuki , K. , Yaki , Y. and Mukaiyama , T. 1981 . Chemistry Lett. , : 1529
  • Dziewiszek , K. , Chmielewski , M. and Zamojski , A. 1982 . Carbohydr. Res. , 104 : C1

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.