Cobalt catalyzed steroid synthesis

Details Cobalt catalyzed steroid synthesis Cobalt catalyzed steroid synthesis

1978-02-21

1980-01-15

Rotman, Alan L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07J 100

Patent

active

041838645

ABSTRACT:
Steroid compounds obtained by co-oligomerization of a side chain functionalized 1,5-hexadiyne with bis(trimethylsilyl)acetylene catalyzed by cyclopentadiene cobalt dicarbonyl, CpCO(CO).sub.2, via intermediate benzocyclobutene formation followed by intramolecular cycloaddition to the sterospecific formation of the steroid nucleus. This constitutes a short steroid synthesis, five steps from commercially available acyclic precursor 1,5-hexadiyne and three steps from 2-methyl-cyclopent-2-enone.

REFERENCES:
Funk and Vollhardt, J. Am. Chem. Society, 98:6755 (1976).
Vollhardt, Accounts of Chemical Research, 10, 1-8 (1977).
Kametani et al., J. Am. Chem. Society, 98:11, May 26, 1976, pp. 3378-3379.
Kametani et al., J. Am. Chem. Society, 99:10, May 11, 1977, pp. 3461-3466.
Funk and Vollhardt, J. of the Chem. Society Chemical Communications, 1976, pp. 833-834.
Hillard and Vollhardt, Angew, Chem. Int. Ed. Engl., 16 (1977), No. 6, p. 399.
Hillard and Vollhardt, J. Am. Chem. Society, 99:4058, Jun. 8, 1977.
Aalbersberg et al., J. Am. Chem. Society, 97:5600, Sep. 17, 1975.
Funk and Vollhardt, J. Am. Chem. Society, 99:5483-5484 (1977).
Chemical and Engineering News, Aug. 15, 1977, p. 21.

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