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Title: A practical chemoenzymic synthesis of the taxol C-13 side chain N-benzoyl-(2R,3S)-3-phenylisoserine
Authors: Da Ming Gou;Yeuk Chuen Liu;Ching Shih Chen
Contributors: 國立臺灣海洋大學:食品科學系
Date: 1993
Issue Date: 2016-12-27T08:19:30Z
Publisher: The Journal of Organic Chemistry
Abstract: Abstract: Taxol (l), an antimicrotubule agent isolated from the bark of Taxus brevifolia,' has recently attracted much attantion because of its efficacy in the treatment of various types of cancer.2 One major impediment to the wide use of tax01 in cancer chemotherapy is its extremely limited availability. Also, chemical complexity has prohibited the commercial production of 1 by total ~ynthesis.~ Thus, a viable approach for the preparation of 1 is to utilize more accessible baccatin 111 (2) or 10-deacetylbaccatin 111 (3) as precursors via a semisynthetic routee.
As the role of the N-benzoyl-(2R,3S)-3-phenylisoserine (4) moiety in the biological activity of 1 became evident? enantioselective synthesis of the (2-13 side chain has been the focus of many investigations.s Here, we describe a facile approach using enzymatically-prepared chiral tram- @-phenylglycidic esters as starting. materials for the synthesis of 4.
Relation: 58(5)
Appears in Collections:[Department of Food Science] Periodical Articles

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