Patent ID: 8193394

Claim:
A method for producing a compound expressed by the formula (5), comprising the following sequential steps of: (a) reacting compounds expressed by the formulae (1), (2) and (3) below in the presence of an acid catalyst to prepare one of a compound expressed by the formula (4) or a mixture of stereoisomers thereof; where, in the formula above, R 1 represents a hydrogen atom, an alkyl group, an acyl group, an alicyclic group, or an aromatic group; R 3 represents at least one substituent selected from a hydrogen atom, an alkyl group, an acyl group, an alicyclic group, an aromatic group, a halogen atom, a hydroxyl group, an alkyloxy group, an acyloxy group, a cyano group, and a nitro group; and n represents an integer of 1 to 4; where, in the formula above, R′ represents at least one substituent selected from a hydrogen atom, an alkyl group, an acyl group, an alicyclic group, an aromatic group, a halogen atom, a hydroxyl group, an alkyloxy group, an acyloxy group, and a cyano group; M represents a silicon atom, a boron atom, a tin atom, a zinc atom, or a magnesium atom; R 4 represents at least one substituent selected from a hydrogen atom, an alkyl group, an acyl group, an alicyclic group, an aromatic group, a halogen atom, a hydroxyl group, an alkyloxy group, an acyloxy group, a cyano group, and a nitro group; m represents an integer of 1 to 5; and p represents an integer of 1 to 4; where, in the formula above, R 2 represents a hydrogen atom, an alkyl group, an acyl group, an alicyclic group, or an aromatic group; R 5 represents at least one substituent selected from a hydrogen atom, an alkyl group, an acyl group, an alicyclic group, an aromatic group, a halogen atom, a hydroxyl group, an alkyloxy group, and an acyloxy group; q represents an integer of 1 to 3; where, in the formula above, R 1 to R 5 , n, m, and q are each the same as those described above; and the wave lines represent a bond of R or S configuration; and (b) preparing one of a compound expressed by the formula (5) below and a mixture of stereoisomers thereof by halogen-induced carbocyclization reaction of one of a compound expressed by the formula (4) and a mixture of stereoisomers thereof; where, in the formula above, R 1 to R 5 , n, m, and q are each the same as those described above; X represents a halogen atom; and the wave lines represent a bond of R or S configuration.