11-Substituted steroids and intermediates

Details 11-Substituted steroids and intermediates 11-Substituted steroids and intermediates

1975-04-28

1977-06-28

Thomas, Jr., James O.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260631R, 260614R, 260615R, 260348C, 260348A, 260488H, 260486R, 260327M, 2603409, 2603407, 260611R, 26039745, C07C 3506

Patent

active

040325792

ABSTRACT:
Precursor compounds are provided for use in the synthesis of 11-chalcogensubstituted steroids and nor-steroids, particularly 18-, 19- and A-nor-steroids. The compounds are acyclic or substituted polyenine with the olefinic groups having the proper geometry to provide the natural ring fusions upon cyclization. To initiate cyclization, a chalcogen atom is positioned in relation to a double bond, so that on protonation of the chalcogen atom, the resulting carbocation will interact with the double bond to form a pi bond if the cyclization initiator is carbocyclic and a sigma bond if the cyclization initiator is acyclic. Upon cyclization, it is found that the substituent at C-11 of the resulting steroid is in the alpha position. Various methods are provided for producing the cyclization precursor.

REFERENCES:
patent: 3741987 (1973-07-01), Johnson et al.
patent: 3904698 (1975-09-01), Johnson et al.
Johnson et al., J.A.C.S., vol. 93, No. 17, pp. 4332-4334 (1971).

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