Chinese Journal of Organic Chemistry >
Synthesis of Paclitaxel Side Chain via Multi-Component Reaction and Its Application to the Synthesis of Paclitaxel Analogues
Received date: 2018-07-24
Revised date: 2018-12-17
Online published: 2018-12-21
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21572067, 21332003).
Under the catalysis of Cu(OTf)2, a hydroxy ylide trapping based multi-component reaction using water, diazoacetates, aromatic aldehydes and aromatic amines was successfully carried out to construct α-hydroxy-β-amino acid ester skeleton in one step. The taxol oxazolidine-type side chains were efficiently synthesized after further chemical transformations. Moreover, 14 taxane derivatives were synthesized through esterification of obtained side chains and 7-O-(triethylsilyl) baccatin Ⅲ or 7,10-dimethoxy-10-beacetyl baccatin Ⅲ, and several novel compounds with excellent activity were discovered in the test of anti-tumor activity. In this paper, combining the methodology and application of multi-component reaction, a highly efficient method for synthesizing paclitaxel side chain derivatives was developed, which was applied into the semi-synthesis of paclitaxel analogues. This research provided a new approach to the study of structure-activity relationship and had potential application value.
Sheng Jiajun , Yu Ya'nan , Wang Xin , Qian Yu , Fu Liwu , Zhao Yun , Ma Mingliang , Hu Wenhao . Synthesis of Paclitaxel Side Chain via Multi-Component Reaction and Its Application to the Synthesis of Paclitaxel Analogues[J]. Chinese Journal of Organic Chemistry, 2019 , 39(2) : 377 -389 . DOI: 10.6023/cjoc201806031
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