Synthesis and molecular structure of ethyl [N-tosyl-(R)-prolyloxy]-2(S)-[4-cyano-8,8-ethylenedioxy-5-oxo-5,6,7,8-tetrahydroindolizin-3-yl] acetate, a key intermediate in the total synthesis of (20S)-camptothecins

Yun-Yan Kuang; Fen-Er Chen

doi:10.3390/12112507

Synthesis and molecular structure of ethyl [N-tosyl-(R)-prolyloxy]-2(S)-[4-cyano-8,8-ethylenedioxy-5-oxo-5,6,7,8-tetrahydroindolizin-3-yl] acetate, a key intermediate in the total synthesis of (20S)-camptothecins

Molecules. 2007 Nov 13;12(11):2507-14. doi: 10.3390/12112507.

Authors

Yun-Yan Kuang¹, Fen-Er Chen

Affiliation

¹ Department of Chemistry, Fudan University, Shanghai 200433, People's Republic of China. yykuang@fudan.edu.cn

Abstract

The synthesis of optically active [N-tosyl-(R)-prolyloxy]-2(S)-[4-cyano-8,8-ethylenedioxy-5-oxo-5,6,7,8-tetrahydroindolizin-3-yl] acetate (4a), a key intermediate for the total asymmetric synthesis of 20(S)-camptothecin anticancer drugs, is described. Its structure was characterized by 2D-NMR techniques and the absolute configuration was further confirmed for the first time by X-ray crystal structure analysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetates* / chemical synthesis
Acetates* / chemistry
Camptothecin* / chemical synthesis
Camptothecin* / chemistry
Crystallography, X-Ray
Molecular Conformation
Molecular Structure
Structure-Activity Relationship

Substances

Acetates
Camptothecin