Process for preparation of adjacently disubstituted ketones

Details Process for preparation of adjacently disubstituted ketones Process for preparation of adjacently disubstituted ketones

1980-05-14

1982-02-09

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Antigen, epitope, or other immunospecific immunoeffector

Recombinant or stably-transformed bacterium encoding one or...

560121, 562503, 536103, 424305, 568345, 568346, 568347, 568390, 568391, 568313, 568314, 568315, 556441, 2603457P, 2603458P, 542426, C07C17700, C07C 4569, C07C 4570, C07C 4572

Patent

active

043150322

ABSTRACT:
A novel 7-hydroxyprostaglandin E.sub.1, or a stereoisomer thereof, or a protected derivative thereof, having the following formula: ##STR1## wherein R.sup.8 represents H, CH.sub.3 or C.sub.2 H.sub.5, R.sup.9 represents H or CH.sub.3, R.sup.10 and R.sup.11 are identical or different, and each represents H, tetrahydropyranyl or t-butyldimethylsilyl. Also provided is a process for producing an adjacently disubstituted ketone including the above compounds, i.e. 7-oxoprostaglandin, etc. which comprises reacting an .alpha.,.beta.-unsaturated carbonyl compound with a cuprous salt and an organolithium compound in an aprotic inert organic medium in the presence of trialkylphosphine, the amounts of said cuprous salt and said organolithium compound being substantially equimolar, and reacting the product with a protected acetal derivative of an organic carbonyl compound or an aldehyde in the presence of a Lewis acid, if necessary, followed by reacting the product with a proton donor.

REFERENCES:
patent: 4131738 (1978-12-01), Smith
Tanaka et al., Tetrahedron Letters, 1535 (1975).

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