Olefinically unsaturated substituents at C-11 of steroid cycliza

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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260514L, 2603409AS, 260586R, 2603407, 260327M, 260526R, 260601R, 260580, 260514G, 260397, 2603973, 260632R, 560203, 560190, 560174, 560205, 560192, C07C 3506

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040641856

ABSTRACT:
Compositions are provided as well as methods for preparing the compositions which serve as cyclization precursors for the preparation of C-11 alkenyl substituted steroids and nor-steroids. The alkenyl group may be converted after cyclization to a variety of heterosubstituents to provide heterofunctionalized C-11 steroids and nor-steroids. The compounds are provided having an initiator group, which has a chalcoxy atom in juxtaposition to a double bond, an olefinically unsaturated linking group and a terminating group which acts to from a carbocation which reacts with a nucleophile to provide a stable product. The C-11 substituent is found to provide upon cyclization the alpha-configuration, so that the subject compounds provide a direct route to the difficultly accessible alpha-C-11 substituted steroids, or, if desired, the alpha-configuration can be inverted to the beta-configuration.

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(17), pp. 4332-4334 (1971).
Johnson et al., J.A.C.S., vol. 92(3), pp. 741-742 (1970).

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