Enzymatic preparation of (3R)-cis-3-acetyloxy-4-(1,1-dimethylethyl)-2-azetidinone: a side-chain synthon for an orally active taxane

Add time:08/09/2019    Source:sciencedirect.com

The chiral intermediate (3R)-cis-3-acetyloxy-4-(1,1-dimethylethyl)-2-azetidinone 2 was prepared for the semi-synthesis of the new taxane 5, an orally active anticancer compound. The enantioselective enzymatic hydrolysis of cis-3-acetyloxy-4-(1,1-dimethylethyl)-2-azetidinone 1 to the corresponding undesired (S)-alcohol 3 and unreacted desired 2 was carried out using immobilized lipase PS-30 or BMS lipase. Reaction yields of >48% and enantiomeric excesses of >99% were obtained for the desired 2. Acetoxy β-lactam 2 was converted to hydroxy β-lactam 4 for use in the semisynthesis of 5.

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