使用胍-脲双功能有机催化剂对内酯进行不对称 α-羟化：（20S）喜树碱类似物关键中间体的催化对映选择性合成。
Asymmetric α-hydroxylation of a lactone with vinylogous pyridone by using a guanidine-urea bifunctional organocatalyst: catalytic enantioselective synthesis of a key intermediate for (20S)-camptothecin analogues.
机构信息
Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588 (Japan), Fax: (+81) 42-388-7295.
出版信息
Chemistry. 2014 Jan 7;20(2):591-7. doi: 10.1002/chem.201303633. Epub 2013 Nov 28.
We have developed a catalytic asymmetric synthesis of (S)-4-ethyl-6,6-(ethylenedioxy)-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,10(4H)dione (5 a), a synthetic intermediate for (20S)-camptothecin analogues. A key step in this synthesis is an asymmetric α-hydroxylation of a lactone with a vinylogous pyridone structure (8 a) by using a guanidine-urea bifunctional organocatalyst. The present oxidation was successfully applied to the synthesis of C20-modified derivatives of (+)-C20-desethylbenzylcamptothecin (13).
我们开发了一种（S）-4-乙基-6,6-（亚乙基二氧基）-7,8-二氢-4-羟基-1H-吡喃并[3,4-f]吲哚嗪-3,10（4H）二酮（5a）的催化不对称合成方法，（5a）是（20S）喜树碱类似物的合成中间体。该合成中的关键步骤是使用胍-脲双功能有机催化剂对具有乙烯基吡啶酮结构的内酯（8a）进行不对称α-羟化。目前的氧化反应成功地应用于（+）-C20-去乙基苯甲酰喜树碱（13）的 C20 修饰衍生物的合成。
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