.DELTA..sup.9 (11) -5.alpha.-D-homo-20-keto steroids

Details .DELTA..sup.9 (11) -5.alpha.-D-homo-20-keto steroids .DELTA..sup.9 (11) -5.alpha.-D-homo-20-keto steroids

1976-06-08

1978-06-27

Garner, Vivian

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

204158HA, 260408, 260410, 260456R, 260586E, 260946, 560 1, 560 56, 560 61, 560 71, 560 73, 560100, 560105, 560107, 560122, 560123, 560124, 560125, 560180, 560184, 560185, 560186, 560188, 560192, 560194, 560227, 560228, C07J 6300

Patent

active

040976785

ABSTRACT:
3.alpha.-Hydroxy and 3.alpha.-acyloxy- .DELTA..sup.9(11) -5.alpha.-D-homo-20-ketopregnenes of the formula ##STR1## wherein R is hydrogen or acyl, R.sub.1 is hydrogen or methyl and R.sub.2 is methyl or ethyl, are produced by esterifying a corresponding 3.beta.-hydroxy-5.alpha.-20-keto pregnane of the formula ##STR2## wherein R.sub.1 and R.sub.2 have the values given above, with m-iodo-benzoic acid with inversion of the 3.beta.-oxy group to a 3.alpha.-oxy group; chlorinating the thus-produced 3.alpha.-m-iodobenzoyl ester with dichloroiodobenzene under irradiation; and treating the reaction product with a dehydrohalogenating silver salt. Optionally thereafter, the 3.alpha.-iodobenzoyl group is split off in a conventional manner to produce the corresponding 3.alpha.-hydroxy steroid and optionally the thus-produced 3.alpha.-hydroxy steroid is esterified to produce a desired 3-ester thereof.

REFERENCES:
patent: 3939193 (1976-02-01), Aleg et al.
Breslow et al., J.A.C.S., 96(1974), 1973.
Ibid 96 (1974), 6791.

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