New Enzymatic Two‐Step Cascade Reaction for the Preparation of a Key Intermediate for the Taxol Side‐Chain

• Published in: European Journal of Organic Chemistry
• Main Authors: Forró, Enikő, Fülöp, Ferenc
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2010
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/ejoc.201000262; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.201000262; https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201000262

Abstract Enzymatic strategies are reported for the synthesis of (2 R ,3 S )‐3‐amino‐2‐hydroxy‐3‐phenylpropionic acid ( ee > 98 %), a key intermediate of the side‐chain of Taxol ® , by enzymatic hydrolysis in organic media. The new enzymatic cascade reaction, which took place through Candida antarctica lipase B‐catalysed deacylation followed by lactam ring‐opening of racemic cis ‐3‐acetoxy‐4‐phenylazetidin‐2‐one with H 2 O in i Pr 2 O at 60 °C, resulted in two different enantiopure products ( ee ≥ 98 %), one of them being the desired key intermediate for the side‐chain of Taxol ® .