New Enzymatic Two‐Step Cascade Reaction for the Preparation of a Key Intermediate for the Taxol Side‐Chain
Authors:
- 17 May 2010
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2010 (16) , 3074-3079
Abstract
Enzymatic strategies are reported for the synthesis of (2R,3S)‐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 H2O in iPr2O 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®.Keywords
This publication has 37 references indexed in Scilit:
- Sculpting the β-peptide foldamer H12 helix via a designed side-chain shapeChemical Communications, 2008
- diexo-3-Aminonorbornane-2-carboxylic Acid as Highly Applicable Chiral Source for the Enantioselective Synthesis of HeterocyclesSynlett, 2008
- Diastereo- and Enantioselective Synthesis of Orthogonally Protected 2,4-Diaminocyclopentanecarboxylates: A Flip from β-Amino- to β,γ-DiaminocarboxylatesThe Journal of Organic Chemistry, 2007
- Synthesis of bi- and tricyclic β-lactam libraries in aqueous mediumGreen Chemistry, 2007
- Effects of the Alternating Backbone Configuration on the Secondary Structure and Self-Assembly of β-PeptidesJournal of the American Chemical Society, 2006
- An Efficient Enzymatic Synthesis of Benzocispentacin and Its New Six‐ and Seven‐Membered HomologuesChemistry – A European Journal, 2006
- Application of alicyclic β-amino acids in peptide chemistryChemical Society Reviews, 2006
- Alicyclic β-amino acids in Medicinal ChemistryAmino Acids, 2005
- Electrophilic Bromination of N‐Acylated Cyclohex‐3‐en‐1‐amines: Synthesis of 7‐AzanorbornanesHelvetica Chimica Acta, 2004
- An Enzyme-Initiated Hydroxylation-Oxidation Carbo Diels-Alder Domino ReactionChemistry – A European Journal, 1998