Enantiomerically pure (Z)-β-sulfinyl allylic alcohols of either handedness can be readily prepared from (Z)-β-sulfinyl enones using NaBH4 or DIBAL reductants in the presence of LaCl3 as a chelating agent. A chiral sulfoxide auxiliary induces the remote 1,2-asymmetric reduction (1,4-induction) to afford various chiral allylic alcohols in high yields with excellent stereoselectivities (up to 100% de).

The asymmetric rearrangement of optically active α-sulfinyl enone 1 induced by catalytic DBU and triphenylphosphine gave optically active γ-hydroxy α-enone derivatives (up to 99% ee) in good yield following treatment with aqueous hydrogen peroxide.

Optically active alkane-6,8-diols have been both chemically synthesized and isolated from the flowers of Carthamus tinctorius. These alkane-6,8-diols were synthesized in moderate yields from a chiral β-ketosulfoxide in three steps, and showed inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate-induced ear inflammation in mice. Natural syn-alkane-6,8-diols displayed a weaker effect compared to the non-natural, synthetic anti-alkane-6,8-diols. Furthermore, the anti-inflammatory effect of these alkane-6,8-diols was highly dependent on the length of the main chain.Optically active alkane-6,8-diols were chemically synthesized and isolated from the flowers of Carthamus tinctorius. A modulated yield of alkane-6,8-diols was synthesized from chiral β-ketosulfoxide in three steps and showed inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate-induced ear inflammation in mice.