An improved synthesis of (20S)-camptothecin and its analogue via an asymmetric α-hydroxylation with a chiral organocatalyst

被引：8

作者：

Wang, Xinlong ^{[1
]}

Xu, Lingjun ^{[1
]}

Xiong, Fangjun ^{[1
]}

Wu, Yan ^{[1
]}

Chen, Fener ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2017年 / 28卷 / 06期

关键词：

CATALYTIC ENANTIOSELECTIVE SYNTHESIS; PLANT ANTITUMOR AGENTS; KEY INTERMEDIATE; PRACTICAL SYNTHESIS; HIGHLY EFFICIENT; PART; CAMPTOTHECIN; 20(S)-CAMPTOTHECIN; CYANOSILYLATION; FAMILY;

D O I：

10.1016/j.tetasy.2017.04.013

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An efficient and stereocontrolled synthesis of (20S)-camptothecin and an analogue has been developed. The key feature of this synthesis is the organocatalyzed asymmetric alpha-hydroxylation of the lactone precursor 4 to construct its stereocenter, providing tricyclic hydroxylactone 2 in 90% yield and with 88% enantioselectivity. The precursor 4 was efficiently synthesized from the known pyridine 5 in three steps. (C) 2017 Published by Elsevier Ltd.

引用

页码：843 / 848

页数：6

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