Synthesis of isoflavanes and intermediates thereof
AssigneeSystem Biologie AG
InventorsNikolai Beliaev, Yuri Shafran
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Abstract
Subject of the invention is a method for enantioselective production of an isoflavane from an isoflavone, comprising the steps: (a) selectively reducing the isoflavone, such that the 4-keto group of the isoflavone is converted to a 4-hydroxy group, and the 2,3-double bond of the isoflavone is converted to a 2,3-single bond, thereby obtaining a 4-hydroxy intermediate, and (b) reacting the 4-hydroxy intermediate with a chiral reagent, such that a chiral group is covalently attached to the C4-position of the 4-hydroxy intermediate, thereby obtaining a chiral intermediate. The invention also relates to intermediates of formulae (IV), (V), (VI) and (VII) obtainable in the inventive process.
Claims20
A method for enantioselective production of equol from daidzein, comprising the steps:
- (a) selectively reducing the daidzein, which may have protective groups covalently attached to the hydroxy groups, such that the 4-keto group of the daidzein is converted into a 4-hydroxy group, and the 2,3-double bond of the daidzein is converted to a 2,3-single bond, thereby obtaining a 4-hydroxy intermediate, and
- (b) reacting the 4-hydroxy intermediate with a chiral reagent, such that a chiral group is covalently attached to the C4-position of the 4-hydroxy intermediate, thereby obtaining a chiral intermediate, and
- (c) reacting the chiral intermediate with an amine reagent, such that an amine group is covalently attached to the C4-position, whereas the chiral group is removed from the C4-position, thereby obtaining an amine intermediate.
A compound of any of formulas (IV) to (VII):
- wherein
- PG is a protective group selected from acyl having 1 to 10 carbon atoms;
- alkoxycarbonyl wherein the alkoxy group has 1 to 10 carbon atoms;
- alkyl having 1 to 10 carbon atoms;
- a cyclic group comprising 1 to 20 carbon atoms;
- an ether group having 1 to 10 carbon atoms;
- a diol toluenesulfonyl (tosyl);
- or silyl,
- ChD is a chiral group having 8 to 30 carbon atoms, which has a chiral carbon atom, optionally 1 to 8 heteroatoms;
- and 1 to 5 rings, and
- residue RNR1 is a cyclic amine having 5 to 20 carbon atoms or a non-cyclic dialkylamine, wherein each alkyl group has 1 to 20 carbon atoms, wherein the cyclic amine may comprise one or more heteroatoms.
Dependencies are inferred from the claim text.