A Stereospecific Total Synthesis of α-Santalol

Journal of the American Chemical Society

Volumn 92, Issue 21, 1970, Pages 6314-6320

  Corey, E J ^a   Kirst, H A ^a   Katzenellenbogen, John A ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000705649     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00724a600     Document Type: Article

References (36)

1. For syntheses of α-santalene see (a) E. J. Corey, S. W. Chow, and R. A. Scherrer, J. Amer. Chem. Soc., 79, 5773 (1957), and
2. E. J. Corey and M. F. Semmelhack, J. Amer. Chem. Soc., 89, 2755 (1967).
3. See (a) lanceol: A. Manjarrez, T. Rios, and A. Guzman, Tetrahedron, 20, 333 (1964);
4. valerenic acid: A. Stoll and E. Seebeck, JustusLiebigs Ann. Chem., 603, 158 (1957); and
5. masticadienonic acid: S. Corsano and E. Mincione, Tetrahedron Lett., 2377 (1965).
6. E. J. Corey and H. Yamamoto, J. Amer. Chem. Soc., 92, 226 (1970).
7. R. G. Lewis, D. H. Gustafson, and W. F. Erman, Tetrahedron Lett., 401 (1967).
8. S. Y. Kamat, K. K. Chakravarti, and S. C. Bhattacharyya, Tetrahedron, 23, 4487 (1967).
9. V. M. Sathe, K. K. Chakravarti, M. V. Kadival, and S. C. Bhattacharyya, Indian J. Chem., 4, 393 (1966).
10. J. Colonge, G. Descotes, Y. Bahurel, and A. Menet, Bull. Soc. Chim. Fr., 374 (1966).
11. E. J. Corey, J. A. Katzenellenbogen, and G. H. Posner, J. Amer. Chem. Soc., 89, 4245 (1967), and references cited therein.
12. 8 it has been found that the lithium aluminum hydride-aluminum chloride reagent usually produces appreciable amounss of 3-iodo-tranj-allylic alcohols in addition to the 2-iodo alcohols 6; see J. A. Katzenellenbogen, Ph.D. Thesis, Harvard University, Cambridge, Mass., 1969.
13. The corresponding iodide (levorotatory) [E. J. Corey, M. Ohno, S. W. Chow, and R. A. Scherrer, J. Amer. Chem. Soc., 81, 6305 (1959)] could also be used.
14. E. J. Corey and H. A. Kirst, Tetrahedron Lett., 5041 (1968).
15. This useful new route to acetylenes has also been employed in these laboratories in the syntheses of the insect juvenile hormone from Cecropia [E. J. Corey, J. A. Katzenellenbogen, N. W. Gilman, S. A. Roman, and B. W. Erickson, J. Amer. Chem. Soc., 90, 5618 (1968)] and
16. sirenin, the Allomyces sperm attractant [E. J. Corey, K. Achiwa, and J. A. Katzenellenbogen, J. Amer. Chem. Soc., 91, 4318 (1969)].
17. H. M. Schmidt and J. F. Arens, Recl. Trac. Chim. Pays-Bas, 86, 1138 (1967).
18. See G. Stork, P. A. Grieco, and M. Gregson, Tetrahedron Lett., 1393 (1969);
19. J. M. Osbond, J. Chem. Soc., 5270 (1961).
20. R. O. Hutchins, D. Hoke, J. Keogh, and D. Koharski, Tetrahedron Lett., 3495 (1969);
21. H. M. Bell, C. W. Vanderslice, and A. Spehar, J. Org. Chem., 34, 3923 (1969).
22. E. J. Corey and L. S. Hegedus, J. Amer. Chem. Soc., 91, 1233 (1969).
23. M. J. Jorgenson, Tetrahedron Lett., 559 (1962).
24. E. J. Corey and K. Achiwa, Tetrahedron Lett., 1837 (1969);
25. J. Org. Chem., 34, 3667 (1969).
26. S. C. Watson and J. F. Eastham, J. Organometal. Chem., 9, 165 (1967).
27. A. D. Petrov, L. L. Shchukovskaya, and Y. P. Egorov, Dokl. Akad. Nauk SSSR, 93, 293 (1953);
28. Chem. Abstr., 48, 13616 (1954).
29. A. Schaap, L. Brandsma, and J. F. Arens, Revl. Trae. Chim. Bays-Bas, 84, 1200 (1965).
30. The spectra obtained for 18 showed all the characteristic bands of the β-santalene unit as described for β-santalene itself by M. F. Semmelhack, Ph.D. Thesis, Harvard University, 1967.
31. V. Herout, V. Jarolim, and J. Pliva, Collect. Czech, Chem. Commun., 22, 773 (1957).
32. Prepared by hydrogenation of 2-decyn-l-ol with 5% palladium on barium sulfate in pyridine as outlined in L. F. Fieser and M. Fieser, “Reagents for Organic Synthesis,” Vol. I, Wiley, New York, N. Y., 1967, p 566.
33. See also F. Bohlmann, U. Niedballa, and J. Schneider, Chem. Ber., 98, 3010 (1965).
34. cis- and trans-2-chloro-2-nonene have been cleanly separated with this column: E. J. Corey, J. I. Shulman, and H. Yamamoto, Tetrahedron Lett., 447 (1970).
35. K. C. Chan, R. A. Jewell, W. H. Nutting, and H. Rapoport, J. Org. Chem., 33, 3382 (1968).
36. J. A. Katzenellenbogen, Ph.D. Thesis, Harvard University, 1969.