New Enzymatic Two‐Step Cascade Reaction for the Preparation of a Key Intermediate for the Taxol Side‐Chain
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 antar...
| Published in: | European Journal of Organic Chemistry |
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| Main Authors: | , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Wiley
2010
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| Subjects: | |
| 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 |
| Summary: | 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 ® . |
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