Stereochemical Study of the [3,3] Sigmatropic Rearrangement of 1,5-Diene-3-alkoxides. Application to the Stereoselective Synthesis of (±)-Juvabione

Journal of the American Chemical Society

Volumn 102, Issue 2, 1980, Pages 774-782

  Evans, David A ^a   Nelson, John V ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000448986     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00522a056     Document Type: Article

References (35)

1. National Science Foundation Predoctoral Fellow.
2. Evans, D. A.; Golob, A. M. J. Am. Chem. Soc. 1975, 97, 4765.
3. Evans, D. A.; Baillargeon, D. J.; Nelson, J. V. J. Am. Chem. Soc. 1978, TOO, 2242.
4. Seebach, D.; Geiss, K.-H.; Pohmakotr, M. Angew. Chem., Int. Ed. Engl. 1976, 15, 437. Still, W. C. J. Am. Chem. Soc. 1977, 99, 4186.
5. Evans, D. A.; Baillargeon, D. J. Tetrahedron Lett. 1978, 3315, 3319.
6. Prepared from propargyl alcohol by the procedure of L. Brandsma: “Preparative Acetylene Chemistry,” Elsevier: New York, 1971; pp 38 and 172.
7. Mercier, F.; Epsztein, R.; Holand, S. Bull. Soc. Chim. Fr. 1972, 690.
8. Kaiser, E. M. Synthesis 1972, 391.
9. Magoon, E. F.; Slaugh, L. H. Tetrahedron 1967, 23, 4509.
10. Corey, E. J.; Katzenellenbogen, J. A.; Posner, G. H. J. Am. Chem. Soc. 1967, 89,4245. Molloy, B. B.; Hauser, K. L. J. Chem. Soc., Chem. Comrnun. 1968, 1017.
11. Coke, J. L.; Williams, H. J.; Natarajan, S. J. Org. Chem. 1977, 42, 2380.
12. Popov, S.; Carlson, R. M. K.; Wegmann, A.; Djerassi, C. Steroids 1976, 28, 699.
13. Ficini, J.; Touzin, A. M. Tetrahedron Lett. 1972, 2093, 2097.
14. We wish to thank Professor Ficini for spectra of both 13a and 13b and a sample of 13a.
15. Perrin, C. L.; Faulkner, D. J. Tetrahedron Lett. 1969, 2783
16. Doering, W. von E.; Roth, W. R. Tetrahedron 1962, 18, 67. Angew. Chem. 1963, 75, 27.
17. Hansen, H.-J.; Schmid, H. Tetrahedron 1974, 30, 1959. Vittorelli, P.; Hansen, H.-J.; Schmid, H. Hetv. Chim. Acta 1975, 58, 1293. Jolidon, S.; Hansen, H.-J. Hetv. Chim. Acta 1977, 60, 2436. Lythgoe, B.; Metcalfe, D. A. Tetrahedron Lett. 1975, 2447.
18. Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1978, 100, 3435.
19. Trost, B. M.; Taber, D. F.; Alper, J. B. Tetrahedron Lett. 1976, 3857.
20. Flcini, J.; d’Angelo, J.; Noire, J. J. Am. Chem. Soc. 1974, 96, 1213,
21. Bowers, W. S.; Fales, H. M.; Thompson, M. J.; Uebel, E. C. Science 1966, 154, 1020.
22. Nakazaki, M.; Isoe, S. Bull. Chem. Soc., Jpn. 1961, 34, 741; 1963, 36, 1198.
23. Pawson, B. A.; Cheung, H.-C.; Gurbaxani, S.; Saucy, G. J. Chem. Soc., Chem. Commun. 1968, 1057. Blount, J. F.; Pawson, B. A.; Saucy, G. Bull. Chem. Soc., Jpn. 1969, 715. Pawson, B. A.; Cheung, H.-C.; Gurbaxani, S.; Saucy, G. J. Am. Chem. Soc. 1970, 92, 336.
24. Cerny, V.; Dolejs, L.; Labler, L.; Sorm, F.; Slama, K. Tetrahedron Lett. 1967, 1053. Collect. Czech. Chem. Commun. 1967, 32, 3926.
25. Rogers, I. H.; Manville, J. F.; Sahota, T. Can. J. Chem. 1974, 52, 1192. Manville, J. F. Tetrahedron Lett. 1975, 53, 1579. Tetrahedron Lett. 1976, 54, 2365.
26. Sakai, T.; Hlrose, Y. Chem. Lett. 1973, 491.
27. Mori, K.; Matsui, M. Tetrahedron 1968, 24, 3127. Ayyar, K. S.; Rao, G. S. K. Can. J. Chem. 1968, 46, 1467. Birch, A. J.; Macdonald, P. L.; Powell, V. H. J. Chem. Soc. C 1970, 1469. Drabklna, A. A.; Tsizin, Y. S. J. Gen. Chem. USSR (Engl. Transi.) 1973, 44, 422, 691. Trost, B. M.; Tamaru, Y. Tetrahedron Lett. 1975, 3797. Negishi, E.; Sabanski, M.; Katz, J.-J.; Brown, H. C. Tetrahedron 1976, 32, 925.
28. Bunnel, C. A.; Fuchs, P. L. J. Am. Chem. Soc. 1977, 99, 5184.
29. Felix, D.; Müller, R. K.; Horn, U.; Joos, R.; Schreiber, J.; Eschenmoser, A. Helv. Chim. Acta 1972, 55, 1276.
30. Biller, S. A.; Evans, D. A. Unpublished results.
31. Müller, R. K.; Joos, R.; Felix, D.; Schreiber, J.; Wintner, C.; Eschenmoser, A. Org. Synth. 1976, 55, 114.
32. Cason, J.; Prout, F. S. J. Am. Chem. Soc. 1944, 66, 46,
33. Manville, J. F.; Bock, K. Org. Magn. Reson. 1977, 9, 596.
34. Purchased from Ventron/Alfa Inorganics.
35. Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 9, 165.