[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH2:7][CH2:6][C:5]2([C:13]([OH:15])=[O:14])[OH:12].CCCCCCC.C(OCC)(=O)C>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH2:7][CH2:6][C@@:5]2([C:13]([OH:15])=[O:14])[OH:12]The enantiomers of 6-chloro-4-hydroxythiochromane-4-yl-carboxylic acid (1.4 g, 5.7 mmol; from step (iii) above) were separated using chiral chromatography (Kromasil TBB; heptane: ethyl acetate: formic acid) yielding 0.500 g (71%) of the slower moving sub-title compound.
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