Total Synthesis of (-)-Laurenyne. Use of Acetal-Initiated Cyclizations To Prepare Functionalized Eight-Membered Cyclic Ethers

Journal of the American Chemical Society

Volumn 110, Issue 7, 1988, Pages 2248-2256

  Overman, Larry E ^a   Thompson, Andrew S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845279920     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00215a040     Document Type: Article

References (39)

1. For reviews, see: Moore, R. E. In Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. 1, Chapter 2. Erickson, K. K. Tetrahedron Lett, 1983; Vol. 5, p 131. Faulkner, D. J. Natl. Prod. Rep. 1984, 251; 1986, 1.
2. Irie, T.; Suzuki, M.; Masamune, T. Tetrahedron 1968, 24, 4193. Irie, T.; Suzuki, M.; Masamune, T. Tetrahedron Lett. 1965, 1091.
3. Cameron, A. F.; Cheung, K. K.; Ferguson, G.; Robertson, J. M. Chem. Commun. 1965, 638.
4. Prelog, V. Helv. Chim. Acta 1953, 36, 308.
5. Falshaw, C. P.; King, T. J.; Imre, S.; Islimyeli, S.; Thomson, R. H. Tetrahedron Lett. 1980, 4951.
6. Gonzalez, A. G.; Martin, J. D.; Martin, V. S.; Norte, M.; Perez, R.; Ruano, J. Z.; Drexler, S. A.; Clardy, J. Tetrahedron 1982, 38, 1009.
7. Masamune, T.; Matsue, H.; Murase, H. Bull. Chem. Soc. Jpn. 1979, 52, 127. Masamune, T.; Murase, H.; Matsue, H.; Murai, A. Tetrahedron 1979, 52, 135. Murai, A.; Murase, H.; Matsue, H.; Masamune, T. Tetrahedron Lett. 1977, 2507. Masamune, T.; Matsue, H. Chem. Lett. 1975, 895.
8. For recent brief discussion of ring formation, see: Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
9. Overman, L. E.; Blumenkopf, T. A.; Castañeda, A.; Thompson, A. S. J. Am. Chem. Soc. 1986, 108, 3516.
10. Nicolaou, K. C.; McGarry, D. G.; Somers, P. K.; Veale, C. A.; Furst, G. T. J. Am. Chem. Soc. 1987, 109, 2504. (b) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E.; Reddy, K. B. Tetrahedron Lett. 1987, 1501. (c) Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E.; Reddy, K. B.; Marron, B. E.; McGarry, D. G. J. Am. Chem. Soc. 1986, 108, 6800. (d) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1986, 108, 2468.
11. Pirrung, M. E.; Werner, J. A. J. Am. Chem. Soc. 1986, 108, 6060.
12. Schreiber, S. L.; Kelley, S. E. Tetrahedron Lett. 1984, 1757.
13. Carling, R. W.; Holmes, A. B. J. Chem. Soc., Chem. Commun. 1986, 565. (b) Carling, R. W.; Holmes, A. B. Tetrahedron Lett. 1986, 6133. (c) Carling, R. W.; Holmes, A. B. J. Chem. Soc., Chem. Commun. 1986, 325.
14. Cockerill, G. S.; Kocienski, P.; Treadgold, R. J. Chem. Soc., Perkin Trans. 1 1985, 2093. (b) Cockerill, G. S.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1983, 705. (c) Mortimore, M.; Cockerill, G. S.; Kocienski, P.; Treadgold, R. Tetrahedron Lett. 1987, 28, 3747.
15. Heslin, J. C.; Moody, C. J.; Slawin, A. M. Z.; Williams, D. C. Tetrahedron Lett. 1986, 1403. Pornet, J.; Damour, D.; Miginiac, L. Tetrahedron 1986, 42, 2017. (b) For a review of older methods for preparing eight-membered ring ethers, see: Moore, J. A.; Anet, F. A. L. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Vol 7, Chapter 5.19.
16. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974. (b) Catalytic procedure: Hanson, R. M.; Ko, S. Y.; Gao, Y.; Masamune, H.; Klunder, J. M.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
17. Commercially available from Petrarch or Aldrich. (b) This material can be easily prepared on a 50-g scale: Boeckman, R. K., Jr.; Blum, D. M.; Ganem, B.; Halvey, N. Org. Synth. 1980, 58, 152.
18. Eis, M. J.; Wrobel, J. E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693.
19. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
20. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
21. Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136. Sharpless, K. B.; Verhoeven, T. R. Aldrichimica Acta 1979, 12, 63.
22. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
23. Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557.
24. Johnson, W. S.; Collins, J. C., Jr.; Pappo, R.; Rubin, M. B.; Kropp, P. J.; Johns, W. F.; Pike, J. E.; Bartmann, W. J. Am. Chem. Soc. 1963, 85, 1409.
25. Miyasita, M.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772.
26. Vollema, G.; Arens, J. F. Recl. Trav. Chim. des Pays-Bas 1963, 82, 305. Viehe, H. G. Chemistry of Acetylenes; Marcel Dekker: New York, 1969, Chapter 11.
27. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
28. Asato, A. E.; Liu, R. S. H. J. Am. Chem. Soc. 1975, 97, 4128.
29. See, e.g.: Streitwieser, A. Solvoltyic Displacement Reactions; McGraw-Hill: New York, 1962, pp 14–25.
30. Corey, E. J.; Rücker, C. Tetrahedron Lett. 1982, 23, 719.
31. Rossiter, B. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1985; Vol. 5, Chapter 7. Finn, M. G.; Sharpless, K. B. Tetrahedron Lett., Chapter 8.
32. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
33. Other methods have been reported for preparing this functional group. See: Petrezilka, M. Helv. Chim. Acta 1978, 61, 2286. Kozikowski, A. P.; Sorgi, K. L.; Schmiesing, R. J. J. Chem. Soc., Chem. Commun. 1980, 477. We were unable to employ these methods since the requisite mixed acetals could not be formed.
34. Wislicenus, A. Justus Liebigs Ann. Chem. 1891, 192, 111.
35. Hall, H. K., Jr. J. Am. Chem. Soc. 1957, 79, 5444. Overman, L. E.; Lesuisse, D.; Hashimoto, M. Justus Liebigs Ann. Chem. 1983, 105, 5373.
36. Look, G.; Overman, L. E., to be submitted for publication.
37. 2BBr has also bee described: Guindon, Y.; Bernstein, M. A.; Anderson, P. C. Tetrahedron Lett. 1987, 2225.
38. General experimental details have been described: Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115. Capillary GC analyses were done on a 12 ft SE-30 column.
39. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 2647.