Hydrogen Peroxide → HCID 68639742, compound

Participants

Reaction Steps

Compounds 8 were silyl deprotected in parallel with HF/pyridine in THF at 0° C. for 30 minutes according to the reported procedure. The products were purified by flash chromatography (4:1 hexanes:EtOAc to 1:1 hexanes:EtOAc) to give the desilylated products in the following yields: (S,S,S,R) 83%, (S,S,R,R) 67%, (S,R,R,R) 85%, (S,R,S,R) 81%. To hydrolyze the thioester to the free acid, these products were dissolved in THF (40 ml/mmole) in parallel, and a 1:1 mixture of 0.2 N LiOH (aq, 4 eq.) and 30% H2O2 (aq) was added to each. The reactions were stirred at room temperature for 3 hours, then cooled to 0° and quenched with 2N NaHSO3 (aq, 5 mL per ml 30% H2O2). The reactions were extracted with EtOAc, washed with brine, dried over MgSO4, filtered, and concentrated under vacuum to give clean 15 in the following yields: (S,S,S,R)-15 100%, (S,S,R,R)-15 96%, (S,R,R,R)-15 100%, (S,R,S,R)-15 100%.

Provenance & Evidence