PURPOSE: To obtain an ene-yne compound useful as a synthetic intermediate of an active form of a vitamin D3 derivative in an effective manner by reacting an optically active alcohol derivative with an ethylene metal salt and subsequently reducing the obtained reaction product.
CONSTITUTION: An enone compound of formula II is obtained by reacting a compound of formula I (R is H or a blocking group for OH; Y is H or a substituted silyl) with a metal salt of ethylene (e.g. halogenated vinylmagnesium) in a solvent (e.g. THF) at 0-50°C. Subsequently, after blocking or deblocking is optionally carried out for a hydroxy group, the compound of formula II is reduced in a diastereo-selectively by a general method to obtain an ene-yne compound of formula III. Use of a compound of formula III as a raw material enables the easy synthesis of 23-hydroxy(or oxo)vitamin D3 derivative useful as a curing or prophylactic agent to diseases such as osteoporosis and rachitis, which are attributable to abnormalities of absorption, transportation or metabolism of calcium, an anti-tumor agent, etc., without depending on time consuming processes and through such a moderate process as silica gel column chromatography for purification.
| JPH10195004 | OPTICALLY ACTIVE ALCOHOL AND ITS PRODUCTION |
| JP2001002602 | PRODUCTION OF OPTICALLY ACTIVE AROMATIC CARBINOL |
IKEDA MASAHIKO
BARII EMU TOROSUTO
