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

Author:
Liu, Qian, Liu, Minjie, Huang, Guangxin, Chen, Fen-er
Source:
Tetrahedron 2019 v.75 no.18 pp. 2647-2651
ISSN:
0040-4020
Subject:
chemical reactions, chemical structure, organic compounds
Abstract:
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.
Agid:
6335359