Stereospecific Synthesis of 2,3-Dihydro-4H-pyran-4-ones by Hg(II)-Catalyzed Rearrangement of 1-Alkynyl-2,3-epoxy Alcohols

Journal of Organic Chemistry

Volumn 63, Issue 12, 1998, Pages 3798-3799

  Marson, Charles M ^a,c   Harper, Steven ^a,d   Oare, Catriona A ^a   Walsgrove, Timothy ^b  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

^d IRBM   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; MERCURY; PYRAN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DRUG SYNTHESIS; STEREOSPECIFICITY;

EID: 0032511115     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9715837     Document Type: Article

References (34)

1. For general syntheses of tetrahydropyrans, see: (a) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617. (b) Kobayashi, Y.; Kitano, Y.; Takedo, Y.; Sato, F. Tetrahedron 1986, 42, 2937. (c) Evans, D. A.; Rieger, D. L.; Jones, T. K.; Kaldor, S. W. J. Org. Chem. 1990, 55, 6260. (d) Smith, A. B., III; Rivero, R. A.; Hale, K. J.; Vaccaro, H. A. J. Am. Chem. Soc. 1991, 113, 2092. (e) Fukuyama, T.; Wang, C.-L. J.; Kishi, Y.; J. Am. Chem. Soc. 1979, 101, 259. (f) Walba, D. M.; Thurmes, W. N.; Haltiwanger, R. C. J. Org. Chem. 1988, 53, 1046. (g) Danishefsky, S. J.; De Ninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15.
2. For general syntheses of tetrahydropyrans, see: (a) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617. (b) Kobayashi, Y.; Kitano, Y.; Takedo, Y.; Sato, F. Tetrahedron 1986, 42, 2937. (c) Evans, D. A.; Rieger, D. L.; Jones, T. K.; Kaldor, S. W. J. Org. Chem. 1990, 55, 6260. (d) Smith, A. B., III; Rivero, R. A.; Hale, K. J.; Vaccaro, H. A. J. Am. Chem. Soc. 1991, 113, 2092. (e) Fukuyama, T.; Wang, C.-L. J.; Kishi, Y.; J. Am. Chem. Soc. 1979, 101, 259. (f) Walba, D. M.; Thurmes, W. N.; Haltiwanger, R. C. J. Org. Chem. 1988, 53, 1046. (g) Danishefsky, S. J.; De Ninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15.
3. For general syntheses of tetrahydropyrans, see: (a) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617. (b) Kobayashi, Y.; Kitano, Y.; Takedo, Y.; Sato, F. Tetrahedron 1986, 42, 2937. (c) Evans, D. A.; Rieger, D. L.; Jones, T. K.; Kaldor, S. W. J. Org. Chem. 1990, 55, 6260. (d) Smith, A. B., III; Rivero, R. A.; Hale, K. J.; Vaccaro, H. A. J. Am. Chem. Soc. 1991, 113, 2092. (e) Fukuyama, T.; Wang, C.-L. J.; Kishi, Y.; J. Am. Chem. Soc. 1979, 101, 259. (f) Walba, D. M.; Thurmes, W. N.; Haltiwanger, R. C. J. Org. Chem. 1988, 53, 1046. (g) Danishefsky, S. J.; De Ninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15.
4. For general syntheses of tetrahydropyrans, see: (a) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617. (b) Kobayashi, Y.; Kitano, Y.; Takedo, Y.; Sato, F. Tetrahedron 1986, 42, 2937. (c) Evans, D. A.; Rieger, D. L.; Jones, T. K.; Kaldor, S. W. J. Org. Chem. 1990, 55, 6260. (d) Smith, A. B., III; Rivero, R. A.; Hale, K. J.; Vaccaro, H. A. J. Am. Chem. Soc. 1991, 113, 2092. (e) Fukuyama, T.; Wang, C.-L. J.; Kishi, Y.; J. Am. Chem. Soc. 1979, 101, 259. (f) Walba, D. M.; Thurmes, W. N.; Haltiwanger, R. C. J. Org. Chem. 1988, 53, 1046. (g) Danishefsky, S. J.; De Ninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15.
5. For general syntheses of tetrahydropyrans, see: (a) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617. (b) Kobayashi, Y.; Kitano, Y.; Takedo, Y.; Sato, F. Tetrahedron 1986, 42, 2937. (c) Evans, D. A.; Rieger, D. L.; Jones, T. K.; Kaldor, S. W. J. Org. Chem. 1990, 55, 6260. (d) Smith, A. B., III; Rivero, R. A.; Hale, K. J.; Vaccaro, H. A. J. Am. Chem. Soc. 1991, 113, 2092. (e) Fukuyama, T.; Wang, C.-L. J.; Kishi, Y.; J. Am. Chem. Soc. 1979, 101, 259. (f) Walba, D. M.; Thurmes, W. N.; Haltiwanger, R. C. J. Org. Chem. 1988, 53, 1046. (g) Danishefsky, S. J.; De Ninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15.
6. For general syntheses of tetrahydropyrans, see: (a) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617. (b) Kobayashi, Y.; Kitano, Y.; Takedo, Y.; Sato, F. Tetrahedron 1986, 42, 2937. (c) Evans, D. A.; Rieger, D. L.; Jones, T. K.; Kaldor, S. W. J. Org. Chem. 1990, 55, 6260. (d) Smith, A. B., III; Rivero, R. A.; Hale, K. J.; Vaccaro, H. A. J. Am. Chem. Soc. 1991, 113, 2092. (e) Fukuyama, T.; Wang, C.-L. J.; Kishi, Y.; J. Am. Chem. Soc. 1979, 101, 259. (f) Walba, D. M.; Thurmes, W. N.; Haltiwanger, R. C. J. Org. Chem. 1988, 53, 1046. (g) Danishefsky, S. J.; De Ninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15.
7. For general syntheses of tetrahydropyrans, see: (a) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617. (b) Kobayashi, Y.; Kitano, Y.; Takedo, Y.; Sato, F. Tetrahedron 1986, 42, 2937. (c) Evans, D. A.; Rieger, D. L.; Jones, T. K.; Kaldor, S. W. J. Org. Chem. 1990, 55, 6260. (d) Smith, A. B., III; Rivero, R. A.; Hale, K. J.; Vaccaro, H. A. J. Am. Chem. Soc. 1991, 113, 2092. (e) Fukuyama, T.; Wang, C.-L. J.; Kishi, Y.; J. Am. Chem. Soc. 1979, 101, 259. (f) Walba, D. M.; Thurmes, W. N.; Haltiwanger, R. C. J. Org. Chem. 1988, 53, 1046. (g) Danishefsky, S. J.; De Ninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15.
8. For syntheses of tetrahydropyrans by the ring closure of 4,5-epoxy alcohols, see: (a) Adiwijaja, G.; Florke, H.; Kirschning, A.; Schaumann, E. Tetrahedron Lett. 1995, 36, 8771. (b) Fujiwara, K.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1995, 36, 8063. (c) Suzuki, T.; Sato, O.; Hirama, M. Tetrahedron Lett. 1990, 31, 4747.
9. For syntheses of tetrahydropyrans by the ring closure of 4,5-epoxy alcohols, see: (a) Adiwijaja, G.; Florke, H.; Kirschning, A.; Schaumann, E. Tetrahedron Lett. 1995, 36, 8771. (b) Fujiwara, K.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1995, 36, 8063. (c) Suzuki, T.; Sato, O.; Hirama, M. Tetrahedron Lett. 1990, 31, 4747.
10. For syntheses of tetrahydropyrans by the ring closure of 4,5-epoxy alcohols, see: (a) Adiwijaja, G.; Florke, H.; Kirschning, A.; Schaumann, E. Tetrahedron Lett. 1995, 36, 8771. (b) Fujiwara, K.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1995, 36, 8063. (c) Suzuki, T.; Sato, O.; Hirama, M. Tetrahedron Lett. 1990, 31, 4747.
11. For isolation and/or structural elucidation of tetrahydropyrans, see: (a) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R.; Schmidt, J. M.; Hooper, J. N. A. J. Org. Chem. 1993, 58, 1302. (b) Lynn, D. G.; Phillips, N. J.; Hutton, W. C.; Shabanowitz, J.; Fennell, D. I.; Cole R. J. J. Am. Chem. Soc. 1982, 104, 7319.
12. For isolation and/or structural elucidation of tetrahydropyrans, see: (a) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R.; Schmidt, J. M.; Hooper, J. N. A. J. Org. Chem. 1993, 58, 1302. (b) Lynn, D. G.; Phillips, N. J.; Hutton, W. C.; Shabanowitz, J.; Fennell, D. I.; Cole R. J. J. Am. Chem. Soc. 1982, 104, 7319.
13. For syntheses of tetrahydropyrans by the ring closure of 5-alkenols, see: Evans, D. A.; Bender, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506. (b) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706.
14. For syntheses of tetrahydropyrans by the ring closure of 5-alkenols, see: Evans, D. A.; Bender, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506. (b) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706.
15. For syntheses of dihydro-4H-pyran-4-ones, see: (a) Mori, K.; Ebata, T. Tetrahedron 1986, 42, 4685. (b) Manker, D. C.; Faulkner, D. J. J. Org. Chem. 1989, 54, 5374. (c) Mori, K.; Kisida, H. Tetrahedron 1986, 42, 5281. (d) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (e) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716. (f) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 2, 273. (g) Paterson, I.; Osborne, S. Tetrahedron Lett. 1990, 31, 2213. (h) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
16. For syntheses of dihydro-4H-pyran-4-ones, see: (a) Mori, K.; Ebata, T. Tetrahedron 1986, 42, 4685. (b) Manker, D. C.; Faulkner, D. J. J. Org. Chem. 1989, 54, 5374. (c) Mori, K.; Kisida, H. Tetrahedron 1986, 42, 5281. (d) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (e) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716. (f) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 2, 273. (g) Paterson, I.; Osborne, S. Tetrahedron Lett. 1990, 31, 2213. (h) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
17. For syntheses of dihydro-4H-pyran-4-ones, see: (a) Mori, K.; Ebata, T. Tetrahedron 1986, 42, 4685. (b) Manker, D. C.; Faulkner, D. J. J. Org. Chem. 1989, 54, 5374. (c) Mori, K.; Kisida, H. Tetrahedron 1986, 42, 5281. (d) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (e) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716. (f) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 2, 273. (g) Paterson, I.; Osborne, S. Tetrahedron Lett. 1990, 31, 2213. (h) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
18. For syntheses of dihydro-4H-pyran-4-ones, see: (a) Mori, K.; Ebata, T. Tetrahedron 1986, 42, 4685. (b) Manker, D. C.; Faulkner, D. J. J. Org. Chem. 1989, 54, 5374. (c) Mori, K.; Kisida, H. Tetrahedron 1986, 42, 5281. (d) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (e) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716. (f) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 2, 273. (g) Paterson, I.; Osborne, S. Tetrahedron Lett. 1990, 31, 2213. (h) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
19. For syntheses of dihydro-4H-pyran-4-ones, see: (a) Mori, K.; Ebata, T. Tetrahedron 1986, 42, 4685. (b) Manker, D. C.; Faulkner, D. J. J. Org. Chem. 1989, 54, 5374. (c) Mori, K.; Kisida, H. Tetrahedron 1986, 42, 5281. (d) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (e) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716. (f) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 2, 273. (g) Paterson, I.; Osborne, S. Tetrahedron Lett. 1990, 31, 2213. (h) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
20. For syntheses of dihydro-4H-pyran-4-ones, see: (a) Mori, K.; Ebata, T. Tetrahedron 1986, 42, 4685. (b) Manker, D. C.; Faulkner, D. J. J. Org. Chem. 1989, 54, 5374. (c) Mori, K.; Kisida, H. Tetrahedron 1986, 42, 5281. (d) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (e) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716. (f) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 2, 273. (g) Paterson, I.; Osborne, S. Tetrahedron Lett. 1990, 31, 2213. (h) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
21. For syntheses of dihydro-4H-pyran-4-ones, see: (a) Mori, K.; Ebata, T. Tetrahedron 1986, 42, 4685. (b) Manker, D. C.; Faulkner, D. J. J. Org. Chem. 1989, 54, 5374. (c) Mori, K.; Kisida, H. Tetrahedron 1986, 42, 5281. (d) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (e) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716. (f) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 2, 273. (g) Paterson, I.; Osborne, S. Tetrahedron Lett. 1990, 31, 2213. (h) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
22. For syntheses of dihydro-4H-pyran-4-ones, see: (a) Mori, K.; Ebata, T. Tetrahedron 1986, 42, 4685. (b) Manker, D. C.; Faulkner, D. J. J. Org. Chem. 1989, 54, 5374. (c) Mori, K.; Kisida, H. Tetrahedron 1986, 42, 5281. (d) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (e) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716. (f) Danishefsky, S. J. Chemtracts: Org. Chem. 1989, 2, 273. (g) Paterson, I.; Osborne, S. Tetrahedron Lett. 1990, 31, 2213. (h) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
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26. All new compounds have been fully characterized (see the Supporting Information). Configurations depicted refer to racemic materials. For further details see the Supporting Information.
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28. General procedure for the preparation of dihydropyranones 2: To a stirred solution of the epoxy alcohol 1 (1.5 mmol) in propanone (30 mL; HPLC grade) at 20 °C was added 0.25 mL of a freshly prepared Hg(II) solution, made by dissolving yellow mercury(II) oxide in dilute sulfuric acid, such that a stock solution 0.1 M in mercury(II) and 2.5 vol % of sulfuric acid was obtained. The optimum time of the reaction (TLC monitoring) was typically between 5 and 20 min.
29. Marson, C. M.; Benzies, D. W. M.; Hobson, A. D. Tetrahedron 1991, 47, 5491. This paper provides an explanation and definition of syn and anti as used herein.
30. Marson, C. M.; Harper, S.; Wriggles worth, R. J. Chem. Soc., Chem. Commun. 1994, 1879.
31. The epimers of le were separated and separately treated with aqueous acidic Hg(II), each isomer affording the same dihydropyranone 2e.
32. Marson, C. M.; Walker, A. J.; Pickering, J.; Hobson, A. D.; Wrigglesworth, R.; Edge, S. J. J. Org. Chem. 1993, 58, 5944.
33. Marson, C. M.; Harper, S.; Walker, A. J.; Pickering, J.; Campbell, J.; Wrigglesworth, R.; Edge, S. J. Tetrahedron 1993, 49, 10339.
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