Process for the stereoselective preparation of 5-substituted delta-lactones and use thereof
AssigneeHoechst Aktiengesellschaft
InventorsPeter Hammann, Susanne Grabley, Ernold Granzer, Yvonne Romeyke
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Abstract
A process for the stereoselective preparation of 5-substituted .delta.-lactones of the formulae Ia, Ib, Ic and Id ##STR1## in which R.sup.1 is a straight-chain or branched alkyl or alkenyl group or methylhydroxy, novel 5-substituted .delta.-lactones and novel intermediates, and use thereof as pharmaceuticals having cholesterol synthesis-inhibiting action, fragrances and flavorings is described.
Claims7
A process for the preparation of 5-substituted 3R, 5R and 3R, 5S .delta.-lactones of the formula Ia or Ib ##STR17## in which R.sup.1 is a straight-chain or branched alkyl group having 3 to 15 carbon atoms or a straight-chain or branched alkenyl group having 3 to 15 carbon atoms and 1 to 7 C--C double bonds, which comprises
- a) disastereoselectively reducing a compound of the formula IIa ##STR18## to a compound of the formula IIIa or IIIb ##STR19## b) regioselectively oxidizing to a compound of the formula Ia or Ib ##STR20## and, optionally, when R.sup.1 is a straight-chain or branched alkenyl group,
- c) hydrogenating the double bonds in the alkylene chain.
A process for the preparation of 5-substituted 3S, 5S and 3S, 5R .delta.-lactones o the formula Ic or Id ##STR21## in which R.sup.1 is a straight-chain or branched alkyl group having 3 to 15 carbon atoms or a straight-chain or branched alkenyl group having 3 to 15 carbon atoms and 1 to 7 C--C double bonds, which comprises
- a) acetalating a compound of the formula IIa ##STR22## to give a compound of the formula IVa or IVb ##STR23## b) oxidizing to give a compound of the formula V ##STR24## c) disastereoselectively reducing to a compound of the formula IVc ##STR25## d) deacetalating to to give a compound of the formula IIb ##STR26## e) diasteroeselectively reducing to a compound of the formula IIIc or IIId ##STR27## f) regioselectively oxidizing to a compound of the formula Ic or Id ##STR28## and, optionally, when R.sup.1 is a straight-chain or branched alkenyl group,
- g) hydrogenating the double bonds in he alkylene chain.
A process for the preparation of 5-substituted 3R, 5R, 3R, 5S, 3S, 5S and 3S, 5R .delta.-catones of the formula Ia, Ib, Ic or Id ##STR29## in which R.sup.1 is CH.sub.2 OH, which comprises a) reacting a compound of the formula Ia, Ib, Ic or Id ##STR30## in which R.sup.1 is a straight-chain or branched alkyl group having 3to 15 carbon atoms or a straight-chain or branched alkenyl group having 3 to 15 carbon atoms and 1 to 7 C--C double bonds, with a compound of the formula R.sup.3 --O.sup.-, in which R.sup.3 is an alkyl group having 1 to 5 carbon atoms or a tertiary butyl group, to give a compound of the formula Va, Vb, Vc, or Vd ##STR31## b) ketalizing with acetone or dimethyoxy propane to give a compound of the formula VIa, VIb, VIc or VId ##STR32## c) oxidizing with ozone to give a compound o the formula VIIa, VIIb, VIIc or VIId ##STR33## and d) cleaving with acid to give a compound of the formula Ia, Ib, Ic or Id ##STR34## in which R.sup.1 is a CH.sub.2 OH group.
Dependencies are inferred from the claim text.