Prins cyclization to tetrahydrofuran units of polyether antibiotics: Remarkable siloxy effect for stereocontrolled cyclization

Tetrahedron

Volumn 52, Issue 21, 1996, Pages 7287-7296

  Mikami, Koichi ^a   Shimizu, Masaki ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POLYETHER ANTIBIOTIC AGENT; TETRAHYDROFURAN DERIVATIVE;

CONFERENCE PAPER; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029932739     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00252-9     Document Type: Conference Paper

References (41)

1. Reviews: (a) Semple, J. E.; Joullie, M. M. Heterocycles 1980, 14, 1825-1870.
2. (b) Bartlett, P. A. "Olefin Cyclization Processes That Form Carbon-Heteroatom Bonds" In Asymmetric Synthesis; J. D. Morrison, Ed.; Academic Press: New York, 1984; Vol. 3; pp 411-454.
3. (c) Boivin, T. L. B. Tetrahedron 1987, 43, 3309-3362.
4. (d) Harding, K. E.; Tiner, T. H. "Electrophilic Heteroatom Cyclizations" In Comprehensive Organic Synthesis; B. M. Trost and I. Fleming, Ed.; Pergamon: Oxford, 1991; Vol. 4; pp 363-421.
5. (e) Harmange, J.-C.; Figadère, B.Tetrahedron:Asymmetry 1993, 4, 1711-1754.
6. (f) Koert, U. Synthesis 1995, 115-132.
7. Reviews on ene reactions: (a) Hoffmann, H. M. R. Angew. Chem. Int. Ed. Engl. 1969, 8, 556-577.
8. (b) Keung, E. C.; Alper, H. J. Chem. Ed. 1972, 49, 97-100.
9. (c) Oppolzer, W.; Snieckus, V. Angew. Chem. Int. Ed. Engl. 1978, 17, 476-486.
10. (d) Snider, B. B. Acc. Chem. Res. 1980, 13, 426-432.
11. (e) Fujita, Y.; Suzuki, S.; Kanehira, K. J. Synth. Org. Chem., Jpn. 1983, 41, 1152-1167.
12. (f) Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984.
13. (g) Dubac, J.; Laporterie, A. Chem. Rev. 1987, 87, 319-334.
14. (h) Carruthers, W. "The Ene Reaction" In Cycloaddition Reactions in Organic Synthesis Pergamon Press: Oxford, 1990; pp 241-268.
15. (i) Snider, B. B. In Comprehensive Organic Synthesis; B. M. Trost and I. Fleming, Ed.; Pergamon: Oxford, 1991; Vol. 2; pp 527-561.
16. (j) Snider, B. B. In Comprehensive Organic Synthsis; B. M. Trost and I. Fleming, Ed.; Pergamon: Oxford, 1991; Vol. 5; pp 1-27.
17. Our reviews on carbonyl-ene reactions: (a) Mikami, K.; Terada, M.; Shimizu, M.; Nakai, T. J. Synth. Org. Chem., Jpn. 1990, 48, 292-303.
18. (b) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050.
19. (c) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255-265.
20. (d) Mikami, K. "Supramolecular Chemistry in Asymmetric Carbonyl-Ene Reactions" In Advances in Aymmetric Synthesis; Hassner, A.Ed.; JAI Press: Greenwich Conneticut 1995; vol 1; pp1-44.
21. Review: Adams, D. R.; Bhatnagar, S. P. Synthesis 1977, 661-672.
22. For leading references, see: (a) Semmelhack, M. F.; Kim, C.; Zhang, N.; Bodurow, C.; Sanner, M.; Dobler, W.; Meier, M. Pure & Appl. Chem. 1990, 62, 2035-2040.
23. (b) Semmelhack, M. F.; Epa, W. R. Tetrahedron Lett. 1993, 34, 7205.
24. For our preliminary communication, see: Mikami, K.; Shimizu, M. Tetrahedron Lett. 1992, 33, 6315-6318. Unfortunately however, no tetrahydropyran formation was observed with trishomoallylic silyl ethers.
25. Recently, Overman reported the "intramolecular Prins cyclization" followed by the pinacol rearrangement to the 3-acyltetrahydrofurans: (a) Overman, L. E. "Cationic Cyclization Reactions Terminated by Pinacol Rearrangements" In Selectivities in Lewis Acid Promoted Reactions; D. Schinzer, Ed.; Kluwer Academic Publishers: Dordrecht, 1989; Vol. 289; pp 1-20.
26. (b) Overman, L. E. Acc. Chem. Res. 1992, 25, 352-359.
27. Mead, K. T.; Yang, H.-L. Tetrahedron Lett. 1989, 30, 6829-6832.
28. Yamamoto, K.; Ohta, O.; Tsuji, J. Chem. Lett. 1979, 713-716.
29. Bartlett, P. A. Tetrahedron 1980, 36, 1-36.
30. Eliel, E. L.; Rao, V. S.; Pietrusiewicz, K. M. Org. Magn. Reson. 1979, 12, 461-466.
31. (a) Tsuneya, T.; Ishihara, M.; Shiota, H.; Shiga, M. Agric. Biol. Chem. 1983, 47, 2495-2502.
32. (b) Nishida, Y.; Ohrui, H.; Meguro, H. Agric. Biol. Chem. 1983, 47, 2969-2971.
33. For synthesis: (c) Andersson, P. G.; Bäckvall, J. J. Org. Chem. 1991, 56, 5349-5353.
34. Rychnovsky, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963-3964.
35. (a) Heemans, V.; Francke, W. Naturwissenshaften 1976, 63, 344.
36. (b) Vite, J. P.; Francke, W. Naturwissenschaften 1976, 63, 550-555.
37. (c) Bloch, R.; Bortolussi, M.; Girard, C.; Seek, M. Tetrahedron 1992, 48, 453-462.
38. (a) Guindon, Y.; Yoakim, C.; Bernstein, M. A.; Morton, H. E. Tetrahedron Lett. 1985, 26, 1185-1188.
39. (b) Yadav, V. K.; Fallis, A. G. J. Org. Chem. 1986, 51, 3372-3374.
40. (c) Guindon, Y.; Therien, M.; Girard, Y.; Yoakim, C. J. Org. Chem. 1987, 52, 1680-1686.
41. (d) Amouroux, R.; Jatczak, M.; Chastrette, M. Bull. Soc. Chim. Fr. 1987, 505-510.