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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 (CC BY 3.0).
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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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