A Cobalt-Catalyzed Steroid Synthesis

Journal of the American Chemical Society

Volumn 99, Issue 16, 1977, Pages 5483-5484

  Funk, Raymond L ^a   Vollhardt, K Peter C ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT; ESTRANE DERIVATIVE;

CATALYSIS; LETTER; SYNTHESIS;

CATALYSIS; COBALT; ESTRENES;

EID: 0017765836     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00458a044     Document Type: Letter

References (16)

1. A. A. Akhrem and Y. A. Titov, “Total Steroid Synthesis”, Plenum Press, New York, N.Y., 1970; K. Nakanlshi In K. Nakanishl, T. Goto, S. ltô, S. Natori, and S. Nozoe, Ed., “Natural Products Chemistry”, Vol. 1, Academic Press, New York, N.Y., 1974, Chapter 6.
2. R. L. Funk and K. P. C. Vollhardt, J. Am. Chem. Soc., 98, 6755 (1976); see also W. G. L. Aalbersberg, A. J. Barkovlch, R. L. Funk, R. L. Hlllard III, and K. P. C. Vollhardt, see also W. G. L. Aalbersberg, A. J. Barkovlch, R. L. Funk, R. L. Hlllard III, and K. P. C. Vollhardt,., 97,5600 (1975);
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7. I. J. Rinkes, Recl. Trav. Chim. Pays-Bas, 57,176 (1938);
8. A. M. Gaddls and L. W. Butz, J. Am. Chem. Soc., 69, 1203 (1947). 1 can also be prepared from 2-methylcyclopentane-1,3-dione via 3-ethoxy-2-methyl-2-cyclo-pentenone followed by reduction with diisobutylaluminum hydride and acidic workup, in a procedure adapted from W. F. Gannon and H. O. House, “Organic Syntheses”, Collect. Vol. V, Wiley, New York, N.Y., 1973, p 294.
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10. See also T. A. Wittstruck and K. I. H. Williams, J. Org. Chem., 38, 1542 (1973).
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12. T. Kametani, Y. Hirai, F. Satoh, and K. Fukumoto, J. Chem. Soc., Chem. Commun., 16 (1977);
13. W. Oppolzer, Angew. Chem., 89,10 (1977); Angew. Chem., Int. Ed. Engl., 16, 10(1977).
14. Oxygenated derivatives of the estrone type should be available via oxidative cleavage of the arylsilicon bond, as demonstrated for simple arylsllanes : J. R. Kalman, J. T. Pinhey, and S. Sternhell, Tetrahedron Lett., 5369 (1972).
15. See, for example, R. W. Freerksen, W. E. Pabst, M. L. Raggio, S. A. Sherman, R. R. Wroble, and D. S. Watt, J. Am. Chem. Soc., 99, 1536 (1977).
16. S. Danishefsky and P. Cain, J. Am. Chem. Soc., 98, 4975 (1976); for a cobalt catalyzed route to annelated pyridines, see A. Naiman and K. P. C. Vollhardt, unpublished work.