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

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

Author(s) -

Forró Enikő,

Fülöp Ferenc

Publication year - 2010

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201000262

Subject(s) - enantiopure drug , chemistry , candida antarctica , side chain , enzyme , stereochemistry , hydrolysis , cascade reaction , lipase , enzymatic hydrolysis , enantioselective synthesis , enzyme catalysis , combinatorial chemistry , organic chemistry , catalysis , polymer

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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