Synthesis of (24R)- and (24S)-5,28-Stigmastadien-3β-ol and Determination of the Stereochemistry of Their 24-Hydroxy Analogues, the Saringosterols

Journal of Organic Chemistry

Volumn 48, Issue 26, 1983, Pages 5207-5214

  Catalan, Cesar A N ^a   Kokke, W C M C ^a   Djerassi, Carl ^a   Duque, Carmenza ^b  

^a STANFORD UNIVERSITY   (United States)

^b UNIVERSIDAD NACIONAL DE COLOMBIA   (Colombia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001257041     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00174a011     Document Type: Article

References (28)

1. Fellow of the Consejo Nacional de Investigaciones Científicas y Técnicas de la República Argentina while on leave from the Universidad Nacional de Tucuman, Argentina.
2. Goad, L. J. Pure Appl. Chem. 1981, 53, 837. Djerassi, C.J. Pure Appl. Chem. 1981, 53, 873.
3. Withers, N.W.; Tuttle, R.C.; Goad, L.J.; Goodwin, T.W. Phytochemistry 1979, 18, 71.
4. De Rosa, M.; Mínale, L.; Sodano, G. Experientia 1975 31, 408; Experientia 1976, 32, 1112. Bibolino, L.; Mínale, L.; Sodano, G.J. Chem. Soc, Chem. Coram. 1978, 524. De Stefano, A.; Sodano, G. Experientia 1980, 36, 630.
5. Mínale, L.; Sodano, G. J. Chem. Soc, Perkin Trans. 1 1974, 1888. De Rosa, M.; Mínale, L.; Sodano, G. Experientia 1975, 31, 758. Mínale, L.; Pérsico, D.; Sodano, G. Experientia 1979, 35, 296.
6. Mínale, L.; Riccio, R.; Scalona, O.; Sodano, G.; Fattorusso, E.; Magno, S.; Mayol, L.; Santacroce, C. Experientia 1977, 33, 1550.
7. Catalan, C.A.N.; Thompson, J.E.; Kokke, W.C.M.C.; Djerassi, C. Tetrahedron, in press.
8. Rohmer, M.; Kokke, W.C.M.C.; Fenical, W.; Djerassi, C. Steroids 1980, 35, 219.
9. Eggersdorfer, M., Stanford University, unpublished results.
10. Parke, M.; Dixon, P.S. J. Mar. Biol. As. UK 1976, 56, 527.
11. Kokke, W.C.M.C.; Shoolery, J.N.; Fenical, W.; Djerassi, C., to be published.
12. Ikekawa, N.; Tauda, K.; Morisaki, N. Chem. Ind. 1966, 1179.
13. Steele, J.A.; Mosettig, E. J. Org. Chem. 1963, 28, 571.
14. Fujimoto, Y.; Moraaaki, M.; Ikekawa, N. J. Chem. Soc, Perkin Trans 1 1975, 2302.
15. Djerassi, C.; Theobald, N.; Kokke, W.C.M.C.; Pak, C.S.; Carlson, R.M.K. Pure Appl. Chem. 1979, 51, 1815.
16. Wyllie, S.G.; Amos, B.A.; Tókés, L. J. Org. Chem. 1977, 42, 725.
17. Fujimoto, Y.; Murakami, K.; Ikekawa, N. J. Org. Chem. 1980, 45, 566.
18. Nicotra, F.; Ronchetti, F.; Russo, G.; Toma, L. Gazz. Chim. Ital. 1980, 110, 151.
19. Knights, B.A. Phytochemistry 1970, 9, 903.
20. Francisco, C.; Combaut, G.; Teste, J.; Tarchini, C.; Djerassi, C. Steroids 1979, 34, 163.
21. Guyot, M.; Davoust, D.; Belaud, C. Tetrahedron Lett. 1982, 23, 1905.
22. Guyot, M.; Durgeat, M. Tetrahedron Lett. 1981, 22, 1391. Gu-natilaka, A.A.L.; Gopichand, Y.; Schmitz, F.J.; Djerassi, C.J. Org. Chem. 1981, 46, 3860 and references therein.
23. Idler, D.R.; Safe, L.M. Steroids 1972, 19, 315.
24. Ratcliffe, R.; Rodehorst, R. J. Org. Chem. 1970, 35, 4000.
25. Corey, E.J.; Suggs, J.W. Tetrahedron Lett. 1975, 2647.
26. Theobald, N.; Wells, R.J.; Djerassi, C. J. Am. Chem. Soc. 1978, 100, 7677.
27. Bligh, E.G.; Dyer, W. J. Can. J. Biochem. Physiol. 1959, 37, 911.
28. Chen, S.-M.; Nakanishi, K.; Atawa, N.; Morisaki, M.; Ikekawa, N.; Shimizu, Y. J. Am. Chem. Soc. 1975, 97, 5297.