Process for manufacture of optically active saturated compounds

A process for manufacturing an optically active saturated compound of the general formula (25):

• ##STR63## wherein R.sub.20 represents a group for protecting a hydroxy group, R.sub.21, R.sub.22 and R.sub.23 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, said process comprising the steps of:
• treating an optically active halogenated compound of the general formula (21b):
• ##STR64## wherein X.sub.20 represents a halogen atom, with a strong base, to obtain an optically active corresponding acetylene alcohol ##STR65## while retaining the chirality;
• reacting said optically active acetylene alcohol compound of the formula (21c) with a benzene halide of the general formula (24):
• ##STR66## wherein X'.sub.20 represents a halogen atom, and R.sub.20, R.sub.21, R.sub.22 and R.sub.23 have the same meanings as above, to obtain an optically active corresponding phenylacetylene compound of the general formula (21d):
• ##STR67## wherein R.sub.20, R.sub.21, R.sub.22 and R.sub.23 have the same meanings as above, while retaining the chirality;
• and
• reducing said optically active phenylacetylene compound of the general formula (21d) to obtain the optically active corresponding saturated compound of the general formula (25) while retaining the chirality.