Tetrahydropyran-2-ols

Details Tetrahydropyran-2-ols Tetrahydropyran-2-ols

1974-03-13

1976-11-02

Raymond, Richard L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260244R, 260307FA, 260327M, 260338, 2603407, 2603409, 2603458, C07D31500

Patent

active

039897249

ABSTRACT:
Stereo-specific total synthesis of steroidal materials. 7-Substituted 3-oxo-1-heptenes or variants thereof are reacted with 2-alkylcycloalkane-1,3-diones yielding 3-substituted 6a .beta.-alkyl-cyclopenta [f] [1] benzopyrans or naphtho [2,1-b] pyrans. These are then subjected to a selective catalytic hydrogenation followed by an introduction of a hydroxy, alkoxy or acyloxy group at the 4a-position to produce a 3-substituted 6a .beta.,4a-hydroxy, alkoxy or acyloxy perhydrocyclopenta [f] [1] benzopyran or perhydro-naphtho [2,1-b] pyran. These latter compounds are then converted into 4- or 5-(3-oxoalkyl)perhydroindene-5-ones or perhydronaphthalene-6-ones which in turn can be converted to known steroidal materials by known methods.

REFERENCES:
patent: 3631039 (1971-12-01), Andrews et al.
patent: 3655695 (1972-04-01), Andrews et al.
patent: 3813417 (1974-05-01), Cohen et al.

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