Synthesis of 16-unsaturated pregnanes from 17-keto steroids

Details Synthesis of 16-unsaturated pregnanes from 17-keto steroids Synthesis of 16-unsaturated pregnanes from 17-keto steroids

1978-05-25

1980-08-05

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602395, 26023955C, 26039745, 2603975, 2603974, C07J 900, C07J 100

Patent

active

042161592

ABSTRACT:
17-Keto steroids (I) in their protected form (IIa or IIb) are reacted with a metalated olefin (VI) to give a 21-aldehyde (IV) which is readily transformed to a 16-unsaturated pregnane (V) which is useful in the production of commercially important substituted corticoids.

REFERENCES:
patent: 3281415 (1966-10-01), Schneider et al.
patent: 3493563 (1970-03-01), Diassi
patent: 3541082 (1970-11-01), Huber
patent: 3631076 (1971-12-01), Clark et al.
patent: 3839369 (1974-10-01), Hofmeister et al.
patent: 4041055 (1977-08-01), Shephard et al.
patent: 4076737 (1978-02-01), Anner et al.
patent: 4089852 (1978-05-01), Nickolson et al.
J. Org. Chemistry, Apr. 14, 1978 article by Ham et al. pp. 1595-1597.
Tetrahedron Letters (1968) No. 8, p. 937.

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