Asymmetric total synthesis of (20S)-Camptothecin using a chiral auxiliary strategy

被引：5

作者：

Liu, Qian ^{[1
,2
]}

Liu, Minjie ^{[1
,2
]}

Huang, Guangxin ^{[1
,2
]}

Chen, Fen-er ^{[1
,2
]}

机构：

[1] Fudan Univ, Dept Chem, Engn Ctr Catalysis & Synth Chiral Mol, Shanghai 200433, Peoples R China

[2] Shanghai Engn Ctr Ind Asymmetr Catalysis Chiral M, Shanghai 200433, Peoples R China

来源：

TETRAHEDRON | 2019年 / 75卷 / 18期

关键词：

Camptothecin; Total synthesis; Heck reaction; Auxiliary-mediated Michael addition; CATALYTIC ENANTIOSELECTIVE SYNTHESIS; ANTITUMOR AGENTS; KEY INTERMEDIATE; CAMPTOTHECIN ALKALOIDS; RADICAL REACTIONS; 20(S)-CAMPTOTHECIN; CYANOSILYLATION; IRINOTECAN; EFFICIENT; FAMILY;

D O I：

10.1016/j.tet.2019.03.028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric eight-step total synthesis of (20S)-camptothecin, starting from the known compound tert-butyl (2-chloroquinolin-3-yl)methylcarbamate, is described. A Heck reaction followed by an intramolecular Michael addition to form the C-ring provides the first key step in this synthesis. The construction of the 20(S) chiral center relies on a chiral auxiliary-mediated Michael addition using (2R,5R)-2-tert-butyl-5-ethyl-1,3-dioxolan-4-one as the auxiliary. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：2647 / 2651

页数：5

共 30 条

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