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

✍ Scribed by Enikő Forró; Ferenc Fülöp

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
422 KB
Volume
2010
Category
Article
ISSN
1434-193X

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✦ Synopsis

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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