C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/369
C07D 303/02 (2006.01) C07D 303/04 (2006.01) C07D 303/16 (2006.01) C07D 303/22 (2006.01) C07D 303/40 (2006.01) C07F 7/18 (2006.01)
Patent
CA 1275413
ABSTRACT OF THE DISCLOSURE Spiro[bicyclo(3.2.0)Heptane-6,2'-oxirane] derivatives of the structural formula: Image wherein X is a hydrocarbon group which is optionally substituted by a C1-4-alkoxy group, a protected hydroxy, protected oxo or protected carboxy group. The hydrocarbon radical serving as the 4-substituent preferably contains 2 to 11 carbon atoms. Especially preferred are straight-chain or branched alkyl groups. The hydrocarbon radical may also be an arylalkyl group such a phenethyl, tolyethyl, phenyl- propyl, phenylbutyl or phenylpentyl. The hydrocarbon radical may also contain a C3-6-cycloalkyl group. The alkoxy group substituted on the X radical can be methoxy, ethoxy, straight-chain or branched propyl or butyl. Conventional substituent groups can be used to protect a hydroxy, oxo, formyl or carboxyl group which may be attached to the X radical against reaction with a methylide reagent such as dimethylsulfonium methylide or dimethyloxosulfonium methylide. The hydroxy group can be protected as C1-4- alkoxy, C6-9-aryloxy, C1-5-alkanoyloxy, C1-16-alkylsulfonyl- oxy, C6-9-arylsulfonyloxy or as a silyl ether derivative, e.g. a tri(C1-5-alkyl)silyloxy or a corresponding phenyl alkyl silyloxy derivative. The carboxyl group can be protected conveniently as a C1-9-alkyl ester, C6-9-aryl- alkyl ester and the like. Aldehydic or oxo groups can be protected as conventional acetals or ketals. The aryl moiety in the protecting group can be phenyl, tolyl, xylyl, cumyl and the like. Such compounds are particularly useful in the preparation of substituted bicyclo(3.2.0)octan-7- ones.
535445
Burnison Chantal
Freeman William P.
Kasha Walter J.
Burnison Chantal
Cbd Corporation
Freeman William P.
Kasha Walter J.
Sim & Mcburney
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