Serofendic acid has been synthesized starting from the known intermediate (I). Allylic oxidation of exo-olefin (I) with SeO2 yields a mixture of alcohols (II) and (III). Hydroboration of isomer (III), followed by oxidative work-up, gives rise to the target syn-diastereoisomer (IV). Inversion of the C15-hydroxyl group in (IV) is then achieved by selective oxidation of the secondary alcohol with NaBrO3/NaHSO3, followed by NaBH(OAc)3 reduction of the resultant ketone (V) to produce diol (VI). Tosylation of diol (VI) takes place at the primary alcohol group, to furnish tosylate (VII).
Displacement of tosylate (VII) with sodium methylsulfide, and simultaneous ester group hydrolysis leads to sulfide (VIII). This is finally oxidized to the corresponding sulfoxide employing Davis oxaziridine.