Sandoz Gmbh

Sandoz Pharm. Corp.

Sandoz Pharmaceuticals Corp.

Charles F Jewell, Jr

James R Wareing

7-Substituted lower alkyl hept-6-enoates and 4-hydroxytetrahydropyran-2-ones bearing 6-olefinic substituents (e.g.,) ethyl erythro-3,5-dihydroxy-7-phenyl-hept-6-enoates are prepared by a multi-step process. The process involves 3-protected-lower alkyl 3,5-dihydroxy-hept-6-enoates, which are obtained by cleaving corresponding 6.alpha.-vinyl-4.beta.-protected hydroxy-tetrahydro 2H-pyran-2-ones. The final products are useful as anti hypercholesteremic agents.

Preparation of lactones

7-Substituted lower alkyl hept-6-enoates and 4-hydroxy-tetrahydropyran-2-ones bearing 6-olefinic substituents (E), (Z), ethyl erythro-3,5-dihydroxy-7-phenyl-hept-6-enates are prepared by a multi-step process involving lower alkyl 3,5-dihydroxy-hept-6-enates. The final products are useful as anti hypercholesteremic agents.

Preparation of olefinic compounds and intermediates thereof

6-trans-indol-2-yl-ethenyl)-4-hydroxy-tetrahydro-2H-pyran-2-ones of formula I are obtained by a multi-step reaction involving the procedure: ##STR1## wherein p.sup.1 is trisubstituted silyl protective group, and Z is a 2-indolyl radical which may be bear at the 4, 5, 6 and 7-positions up to two substituents such as alkyl, alkoxy, halo and CF.sub.3, and at either one the 1 or 3-positions a substituted or unsubstituted phenyl; and at the other an assymetric alkyl, cycloalkyl or aralkyl radical. Compounds I, e.g. (E)-trans-6-[1'-methyl-3'-(4'-fluorophenyl)indol-2'-ylethenyl]3,4,5,6 -tetrahydro-4-hydroxy-2H-pyran-2-one(4R,6S); are useful as anti-atheroselerotic agents.

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Atlanta, GA, United States of America

Charles F Jewell, Jr