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Molecules 2007, 12(11), 2507-2514; doi:10.3390/12112507
Article

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

 and *
Department of Chemistry, Fudan University, Shanghai 200433, People’s Republic of China
* Author to whom correspondence should be addressed.
Received: 24 May 2007 / Revised: 6 August 2007 / Accepted: 6 August 2007 / Published: 13 November 2007
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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 forthe total asymmetric synthesis of 20(S)-camptothecin anticancer drugs, is described. Itsstructure was characterized by 2D-NMR techniques and the absolute configuration wasfurther confirmed for the first time by X-ray crystal structure analysis.
Keywords: Ethyl [N-tosyl-(R)-prolyloxy]-2(S)-[4-cyano-8; 8-ethylenedioxy-5-oxo-5; 6; 7; 8-tetrahydroindolizin-3-yl] acetate; 2D-NMR techniques; X-ray crystal structure; configurational analysis. Ethyl [N-tosyl-(R)-prolyloxy]-2(S)-[4-cyano-8; 8-ethylenedioxy-5-oxo-5; 6; 7; 8-tetrahydroindolizin-3-yl] acetate; 2D-NMR techniques; X-ray crystal structure; configurational analysis.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Kuang, Y.-Y.; Chen, F.-E. 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, 12, 2507-2514.

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