Enantioselective Synthesis of Spiro Ethers and Spiro Ketals via Photoaddition of Dihydro-4-pyrones to Chiral 1,3-Dioxin-4-ones 1

Journal of Organic Chemistry

Volumn 62, Issue 22, 1997, Pages 7629-7636

  Haddad, Nizar ^a   Rukhman, Igor ^a   Abramovich, Zehavit ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000673678     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970816r     Document Type: Article

References (69)

1. For reviews in this area, see: (a) Perron, F.; Albizati, F. Chem. Rev. 1989, 89, 1617. (b) Davies, H. G.; Green, R. H. Chem. Soc. Rev. 1991, 20, 211; 271. (c) Westley, J. W.; Seto, H. J. Antibiotics 1979, 32, 959. For other reviews of polyether antibiotics; see: (d) Hodgson, K. O. Intra Sci. Chem. Rep. 1974, 8, 27. (e) Westley, J. W. Annu. Rep. Med. Chem. 1975, 10, 246. (f) Pressman, B. C. Anna. Rev. Biochem. 1976, 45, 501.
2. For reviews in this area, see: (a) Perron, F.; Albizati, F. Chem. Rev. 1989, 89, 1617. (b) Davies, H. G.; Green, R. H. Chem. Soc. Rev. 1991, 20, 211; 271. (c) Westley, J. W.; Seto, H. J. Antibiotics 1979, 32, 959. For other reviews of polyether antibiotics; see: (d) Hodgson, K. O. Intra Sci. Chem. Rep. 1974, 8, 27. (e) Westley, J. W. Annu. Rep. Med. Chem. 1975, 10, 246. (f) Pressman, B. C. Anna. Rev. Biochem. 1976, 45, 501.
3. For reviews in this area, see: (a) Perron, F.; Albizati, F. Chem. Rev. 1989, 89, 1617. (b) Davies, H. G.; Green, R. H. Chem. Soc. Rev. 1991, 20, 211; 271. (c) Westley, J. W.; Seto, H. J. Antibiotics 1979, 32, 959. For other reviews of polyether antibiotics; see: (d) Hodgson, K. O. Intra Sci. Chem. Rep. 1974, 8, 27. (e) Westley, J. W. Annu. Rep. Med. Chem. 1975, 10, 246. (f) Pressman, B. C. Anna. Rev. Biochem. 1976, 45, 501.
4. For reviews in this area, see: (a) Perron, F.; Albizati, F. Chem. Rev. 1989, 89, 1617. (b) Davies, H. G.; Green, R. H. Chem. Soc. Rev. 1991, 20, 211; 271. (c) Westley, J. W.; Seto, H. J. Antibiotics 1979, 32, 959. For other reviews of polyether antibiotics; see: (d) Hodgson, K. O. Intra Sci. Chem. Rep. 1974, 8, 27. (e) Westley, J. W. Annu. Rep. Med. Chem. 1975, 10, 246. (f) Pressman, B. C. Anna. Rev. Biochem. 1976, 45, 501.
5. For reviews in this area, see: (a) Perron, F.; Albizati, F. Chem. Rev. 1989, 89, 1617. (b) Davies, H. G.; Green, R. H. Chem. Soc. Rev. 1991, 20, 211; 271. (c) Westley, J. W.; Seto, H. J. Antibiotics 1979, 32, 959. For other reviews of polyether antibiotics; see: (d) Hodgson, K. O. Intra Sci. Chem. Rep. 1974, 8, 27. (e) Westley, J. W. Annu. Rep. Med. Chem. 1975, 10, 246. (f) Pressman, B. C. Anna. Rev. Biochem. 1976, 45, 501.
6. For reviews in this area, see: (a) Perron, F.; Albizati, F. Chem. Rev. 1989, 89, 1617. (b) Davies, H. G.; Green, R. H. Chem. Soc. Rev. 1991, 20, 211; 271. (c) Westley, J. W.; Seto, H. J. Antibiotics 1979, 32, 959. For other reviews of polyether antibiotics; see: (d) Hodgson, K. O. Intra Sci. Chem. Rep. 1974, 8, 27. (e) Westley, J. W. Annu. Rep. Med. Chem. 1975, 10, 246. (f) Pressman, B. C. Anna. Rev. Biochem. 1976, 45, 501.
7. For a review of Milbemycin synthesis see: (a) Boeckman, R. K., Jr.; Goldman, S. W. The Total Synthesis of Natural Products; Simon, J., Ed.; Wiley: New York, 1988; Vol. 7, pp 88-92. See also: (b) Crimmins, M. T.; Al-awar, R. S.; Vallin, I. M.; Hollis, W. G.; O'Mahony, R.; Lever, J. G.; Bankaitis, D. M. J. Am. Chem. Soc. 1996, 118, 7513 and references cited therein. (c) Ley, S. V.; Madin, A.; Monck, N. J. T. Tetrahedron Lett. 1993, 34, 7479 and references cited therein. For Avermectin synthesis, see: (d) Ferezou, J. P.; Julia, M.; Li, Y.; Liu, L. W.; Pancrazi, A. Bull. Soc. Chim. Fr. 1995, 132, 428. (e) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Seinick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967. (f) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117. (g) Hanessian, S.; Ugolini, A.; Hodges, P. J.; Beaulieu, P.; Dube, A. C. Pure Appl. Chem. 1987, 59, 299.
8. For a review of Milbemycin synthesis see: (a) Boeckman, R. K., Jr.; Goldman, S. W. The Total Synthesis of Natural Products; Simon, J., Ed.; Wiley: New York, 1988; Vol. 7, pp 88-92. See also: (b) Crimmins, M. T.; Al-awar, R. S.; Vallin, I. M.; Hollis, W. G.; O'Mahony, R.; Lever, J. G.; Bankaitis, D. M. J. Am. Chem. Soc. 1996, 118, 7513 and references cited therein. (c) Ley, S. V.; Madin, A.; Monck, N. J. T. Tetrahedron Lett. 1993, 34, 7479 and references cited therein. For Avermectin synthesis, see: (d) Ferezou, J. P.; Julia, M.; Li, Y.; Liu, L. W.; Pancrazi, A. Bull. Soc. Chim. Fr. 1995, 132, 428. (e) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Seinick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967. (f) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117. (g) Hanessian, S.; Ugolini, A.; Hodges, P. J.; Beaulieu, P.; Dube, A. C. Pure Appl. Chem. 1987, 59, 299.
9. For a review of Milbemycin synthesis see: (a) Boeckman, R. K., Jr.; Goldman, S. W. The Total Synthesis of Natural Products; Simon, J., Ed.; Wiley: New York, 1988; Vol. 7, pp 88-92. See also: (b) Crimmins, M. T.; Al-awar, R. S.; Vallin, I. M.; Hollis, W. G.; O'Mahony, R.; Lever, J. G.; Bankaitis, D. M. J. Am. Chem. Soc. 1996, 118, 7513 and references cited therein. (c) Ley, S. V.; Madin, A.; Monck, N. J. T. Tetrahedron Lett. 1993, 34, 7479 and references cited therein. For Avermectin synthesis, see: (d) Ferezou, J. P.; Julia, M.; Li, Y.; Liu, L. W.; Pancrazi, A. Bull. Soc. Chim. Fr. 1995, 132, 428. (e) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Seinick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967. (f) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117. (g) Hanessian, S.; Ugolini, A.; Hodges, P. J.; Beaulieu, P.; Dube, A. C. Pure Appl. Chem. 1987, 59, 299.
10. For a review of Milbemycin synthesis see: (a) Boeckman, R. K., Jr.; Goldman, S. W. The Total Synthesis of Natural Products; Simon, J., Ed.; Wiley: New York, 1988; Vol. 7, pp 88-92. See also: (b) Crimmins, M. T.; Al-awar, R. S.; Vallin, I. M.; Hollis, W. G.; O'Mahony, R.; Lever, J. G.; Bankaitis, D. M. J. Am. Chem. Soc. 1996, 118, 7513 and references cited therein. (c) Ley, S. V.; Madin, A.; Monck, N. J. T. Tetrahedron Lett. 1993, 34, 7479 and references cited therein. For Avermectin synthesis, see: (d) Ferezou, J. P.; Julia, M.; Li, Y.; Liu, L. W.; Pancrazi, A. Bull. Soc. Chim. Fr. 1995, 132, 428. (e) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Seinick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967. (f) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117. (g) Hanessian, S.; Ugolini, A.; Hodges, P. J.; Beaulieu, P.; Dube, A. C. Pure Appl. Chem. 1987, 59, 299.
11. For a review of Milbemycin synthesis see: (a) Boeckman, R. K., Jr.; Goldman, S. W. The Total Synthesis of Natural Products; Simon, J., Ed.; Wiley: New York, 1988; Vol. 7, pp 88-92. See also: (b) Crimmins, M. T.; Al-awar, R. S.; Vallin, I. M.; Hollis, W. G.; O'Mahony, R.; Lever, J. G.; Bankaitis, D. M. J. Am. Chem. Soc. 1996, 118, 7513 and references cited therein. (c) Ley, S. V.; Madin, A.; Monck, N. J. T. Tetrahedron Lett. 1993, 34, 7479 and references cited therein. For Avermectin synthesis, see: (d) Ferezou, J. P.; Julia, M.; Li, Y.; Liu, L. W.; Pancrazi, A. Bull. Soc. Chim. Fr. 1995, 132, 428. (e) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Seinick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967. (f) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117. (g) Hanessian, S.; Ugolini, A.; Hodges, P. J.; Beaulieu, P.; Dube, A. C. Pure Appl. Chem. 1987, 59, 299.
12. For a review of Milbemycin synthesis see: (a) Boeckman, R. K., Jr.; Goldman, S. W. The Total Synthesis of Natural Products; Simon, J., Ed.; Wiley: New York, 1988; Vol. 7, pp 88-92. See also: (b) Crimmins, M. T.; Al-awar, R. S.; Vallin, I. M.; Hollis, W. G.; O'Mahony, R.; Lever, J. G.; Bankaitis, D. M. J. Am. Chem. Soc. 1996, 118, 7513 and references cited therein. (c) Ley, S. V.; Madin, A.; Monck, N. J. T. Tetrahedron Lett. 1993, 34, 7479 and references cited therein. For Avermectin synthesis, see: (d) Ferezou, J. P.; Julia, M.; Li, Y.; Liu, L. W.; Pancrazi, A. Bull. Soc. Chim. Fr. 1995, 132, 428. (e) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Seinick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967. (f) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117. (g) Hanessian, S.; Ugolini, A.; Hodges, P. J.; Beaulieu, P.; Dube, A. C. Pure Appl. Chem. 1987, 59, 299.
13. For a review of Milbemycin synthesis see: (a) Boeckman, R. K., Jr.; Goldman, S. W. The Total Synthesis of Natural Products; Simon, J., Ed.; Wiley: New York, 1988; Vol. 7, pp 88-92. See also: (b) Crimmins, M. T.; Al-awar, R. S.; Vallin, I. M.; Hollis, W. G.; O'Mahony, R.; Lever, J. G.; Bankaitis, D. M. J. Am. Chem. Soc. 1996, 118, 7513 and references cited therein. (c) Ley, S. V.; Madin, A.; Monck, N. J. T. Tetrahedron Lett. 1993, 34, 7479 and references cited therein. For Avermectin synthesis, see: (d) Ferezou, J. P.; Julia, M.; Li, Y.; Liu, L. W.; Pancrazi, A. Bull. Soc. Chim. Fr. 1995, 132, 428. (e) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Seinick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967. (f) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117. (g) Hanessian, S.; Ugolini, A.; Hodges, P. J.; Beaulieu, P.; Dube, A. C. Pure Appl. Chem. 1987, 59, 299.
14. Mishima, H.; Junya, I.; Muramatsu, S.; Ono, M. J. Antibiotics 1983, 36, 980.
15. Moore, R. E. Marine Natural Products-Chemical and Biological Prespectiues; Scheuer P. J., Ed.; Academic Press: New York, 1981; Vol. 4, Chapter 1. Bhakuni, D. S. J. Sci. Ind. Res. 1995, 54, 702 and references cited therein.
16. Moore, R. E. Marine Natural Products-Chemical and Biological Prespectiues; Scheuer P. J., Ed.; Academic Press: New York, 1981; Vol. 4, Chapter 1. Bhakuni, D. S. J. Sci. Ind. Res. 1995, 54, 702 and references cited therein.
17. Phillips, N. J.; Cole, R. J.; Lynn, D. G. Tetrahedron Lett. 1987, 28, 1619.
18. (a) Kurth, M. J.; Brown, E. G.; Hendra, E.; Hope, H. J. Org. them. 1985, 50, 1115. Smith, A. B., III; Thompson, A. S. J. Org. Chem. 1984, 49, 1469.
19. (a) Kurth, M. J.; Brown, E. G.; Hendra, E.; Hope, H. J. Org. them. 1985, 50, 1115. Smith, A. B., III; Thompson, A. S. J. Org. Chem. 1984, 49, 1469.
20. (b) Schreiber, S. L.; Sommer, T. J.; Satake, K. Tetrahedron Lett. 1985, 26, 17.
21. (c) Mori, K.; Ikuuaki, M. Tetrahedron 1987, 43, 45.
22. (d) Baker, R.; Boyes, A. L.; Swain, C. J. J. Chem. Soc., Perkin Trans. 1, 1990, 1415.
23. (a) Toshima, H.; Goto, T.; Ichihara, A. Tetrahedron Lett. 1995, 36, 3373.
24. (b) Toshima, H.; Goto, T.; Ichihara, A. Tetrahedron Lett. 1994, 35, 4361.
25. (a) Haddad, N.; Abramovich, Z.; Rukhman, I. Tetrahedron Lett. 1996, 37, 3521.
26. (b) Haddad, N.; Abramovich, Z.; Rukhman, I. Recent Research Developments in Organic Chemistry; Pahdalai, S. G.; Ed.; Transworld Research Network: New York, 1997, Vol. 1, 35.
27. Haddad, N.; Abramovich, Z. J. Org. Chem. 1995, 60, 6883.
28. Haddad, N.; Kuzmenkov, I. Tetrahedron Lett. 1993, 34, 6127.
29. For elegant synthetic applications of the intramolecular photoadditions of dioxinones to alkenes, see: Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003.
30. (a) Demuth, M.; Palomer, A.; Sluma, H. D.; Dey, A. K.; Kruger, C.; Tsay, Y. H. Angew, Chem. Int. En. Engl. 1986, 25, 1117.
31. (b) Demuth, M. Pure Appl. Chem. 1986, 58, 1233.
32. (a) Organ, M. G.; Forese, R. D.; Goodard, J. D.; Taylor, N. J.; Lange, G. L. J. Am. Chem. Soc. 1994, 116, 3312.
33. (b) Lange, G. L.; Organ, M. G. Tetrahedron Lett. 1993, 34, 1425.
34. Sato, M.; Abe, Y.; Kaneko, C. Heterocycles 1990, 30, 217.
35. Winkler, J. D.; Hey, J. P.; Hannon, F. J. Heterocycles 1987, 25, 55. Karpcho, A. P. Synthesis 805 (1982).
36. Winkler, J. D.; Hey, J. P.; Hannon, F. J. Heterocycles 1987, 25, 55. Karpcho, A. P. Synthesis 805 (1982).
37. Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082.
38. Curran, D. P.; Heffner, T. A. J. Org. Chem. 1990, 65, 4585.
39. (a) Allylic bromination (NBS + AIBN): Hyp, J.; Dauben, J. R.; McCoy, L. L. J. Am. Chem. Soc. 1959, 81, 4863.
40. (b) Allylic bromination (NBS + M: Dauben, W. G.; Kohler, B.; Roesle, A. J. Org. Chem. 1985, 50, 2007.
41. Sato, M.; Abe, Y.; Kaneko, C. J. Chem. Soc. Perkin Trans. 1 1990, 1779.
42. (a) Sato, M.; Ogasawara, H.; Oi, K.; Kato, T. Chem. Pharm. Bull. 1983, 31, 1896.
43. (b) Huckin, S.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082.
44. (a) Seebach, D.; Zimmermann, J. Helv. Chim. Acta. 1987, 70, 1104.
45. (b) Seebach, D.; Noda, Y. Helv. Chim. Acta. 1987, 70, 2137.
46. (a) Corey, E. J.; Udea, Y.; Ruden, R. A. Tetrahedron Lett. 1975, 16, 4347.
47. (b) Millar, J. G.; Underhill, E. W. J. Org. Chem. 1986, 51, 4726.
48. (a) Winkler, J. D.; Hershberger, P. M. J. Am. Chem. Soc. 1989, 111, 4852.
49. (b) Winkler, J. D.; Hershberger, P. M.; Spiringer, J. P. Tetrahedron Lett. 1986, 27, 5177.
50. For an example of selective Baeyer - Villager oxidation, see: (a) Shishido, K.; Takahashi, K.; Fukumoto, K. J. Org. Chem. 1987, 52, 5704. (b) Baldwin, S. W.; Wilkinson, J. M. Tetrahedron Lett. 1979, 20, 2657.
51. For an example of selective Baeyer - Villager oxidation, see: (a) Shishido, K.; Takahashi, K.; Fukumoto, K. J. Org. Chem. 1987, 52, 5704. (b) Baldwin, S. W.; Wilkinson, J. M. Tetrahedron Lett. 1979, 20, 2657.
52. The relative stereochemical relationship of the stereogenic centers was determined by NOE difference. Determination of these protons resonances carried out by COSY-45, XH-CORR, and JMOD-XH methods and was supported by NOE experiments.
53. Brown, H. C.; Garg, C. P.; Liu, K. T. J. Org. Chem. 1971, 36, 387.
54. 1H-NMR.
55. (a) Haddad, N. The Chemistry of Functional Groups, Supplement A3: The Chemistry of Double-bonded Functional Groups; Patai, S., Eds.; Wiley: New York, 1997; Chapter 13, p 641.
56. (b) Schuster, D. I.; Lem, G.; Caprinidis, N. A. Chem. Rev. 1993, 93, 3.
57. (c) Demuth, M.; Mikhail, G. Synthesis 1989, 145.
58. (d) Becker, D.; Haddad, N. Organic Photochemistry; Padwa, A., Ed.; Dekker press: New York, 1989; Vol. 10, 1.
59. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
60. For determination of similar structures by NMR, c.f.: (a) Becker, D.; Haddad, N. Tetrahedron 1993, 49, 947. (b) Becker, D.; Haddad, N. Isr. J. Chem. 1989, 29, 303.
61. For determination of similar structures by NMR, c.f.: (a) Becker, D.; Haddad, N. Tetrahedron 1993, 49, 947. (b) Becker, D.; Haddad, N. Isr. J. Chem. 1989, 29, 303.
62. Sato, M.; Uehara, F.; Kamaya, H.; Murakami, M.; Kaneko, C.; Furuya, T.; Kurihara, H. J. Chem. Soc., Chem. Commun. 1996, 1063.
63. (a) Seebach, D.; Zuger, M. Helv. Chim. Acta 1982, 65, 495.
64. (b) Seebach, D.; Beck, A. K.; Breitschuh, R.; Job, K. Org. Synth. 1992, 71, 39.
65. (a) Cainelli, G.; Manescalchi, F.; Martelli, G.; Panunzio, M.; Plessi, L. Tetrahedron Lett. 1985, 26, 3369.
66. (b) Griesbeck, A.; Seebach, D. Helv. Chim. Acta 1987, 70, 1320.
67. (c) Seebach, D.; Sutter, M. A.; Weber, R. H.; Zuger, M. F. Org. Synth. 1990, Collect. Vol. VII 1990, 215.
68. Lange, G. L. Organ, M. G.; Roche, M. R. J. Org. Chem. 1992, 57, 6000.
69. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre the coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.