Next Article in Journal
Comparative Study of Regioselective Synthesis of β-Aminoalcohols under Solventless Conditions Catalyzed by Sulfated Zirconia and SZ/MCM-41
Previous Article in Journal
Cyclization-activated Prodrugs
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 *
Received: 24 May 2007; in revised form: 6 August 2007 / Accepted: 6 August 2007 / Published: 13 November 2007
Download PDF [130 KB, uploaded 18 June 2014]
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.

Export to BibTeX |
EndNote


MDPI and ACS Style

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.

AMA Style

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(11):2507-2514.

Chicago/Turabian Style

Kuang, Yun-Yan; Chen, Fen-Er. 2007. "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 12, no. 11: 2507-2514.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert