Total synthesis of 1RS,4SR,5RS,-4-(4,8-dimethyl-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8-dioxab icyclo[3.2.1]octane-1-acetic acid
AssigneeOrtho Pharmaceutical Corporation
InventorsZoltan G. Hajos, Seymour Levine
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Abstract
The synthesis of 1RS,4SR,5RS-4-(4,8-dimethyl-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8-dioxabicy clo[3.2.1]octane-1-acetic acid is described. The bicyclo acetic acid compound is useful as a uteroevacuant agent.
Claims7
The process for the preparation of a compound of the formula ##STR3## which comprises reacting a compound of the formula ##STR4## with methyl 2-lithio-propionate and hydrolyzing the ester to form a compound of the formula ##STR5## reacting the acid with 3-methyl-2-butenyl lithium, reacting the ketone formed with a reducing agent, treating the product formed with aqueous hydrochloric acid and esterifying the hydroxy compound with an esterifying agent to form a compound of the formula ##STR6## reacting the aldehyde with a compound of the formula
- (C.sub.6 H.sub.5).sub.3 P.dbd.CH.sub.2
- reacting the product formed first with borane-THF followed by treatment with an alkali metal hydroxide and hydrogen peroxide, oxidizing the product formed with an oxidizing agent, hydrolyzing the ester with a base and treating the product formed with a mineral acid, wherein R is a lower alkanoyl group having 2-6 carbon atoms and Ms is a mesyl group.
Dependencies are inferred from the claim text.