Total Synthesis of (+)-Amphidinolide A. Structure Elucidation and Completion of the Synthesis
The structure elucidation of (+)-amphidinolide A, a cytotoxic macrolide, has been accomplished by employing a combination of NMR chemical shift analysis and total synthesis. The 20-membered ring of amphidinolide A was formed by a ruthenium-catalyzed alkene−alkyne coupling to forge the C15−C16 bond....
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| Veröffentlicht in: | Journal of the American Chemical Society 2005-10, Vol.127 (39), p.13598-13610 |
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| container_end_page | 13610 |
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| container_issue | 39 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 127 |
| creator | Trost, Barry M Harrington, Paul E Chisholm, John D Wrobleski, Stephen T |
| description | The structure elucidation of (+)-amphidinolide A, a cytotoxic macrolide, has been accomplished by employing a combination of NMR chemical shift analysis and total synthesis. The 20-membered ring of amphidinolide A was formed by a ruthenium-catalyzed alkene−alkyne coupling to forge the C15−C16 bond. Using the reported structure 1 as a starting point, a number of diastereomers of amphidinolide A were prepared. Deviations of the chemical shift of key protons in each isomer relative to the natural material were used as a guide to determine the locations of the errors in the relative stereochemistry. The spectroscopic data for the synthetic and natural material are in excellent agreement. |
| doi_str_mv | 10.1021/ja053365y |
| format | Article |
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Structure Elucidation and Completion of the Synthesis</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>The structure elucidation of (+)-amphidinolide A, a cytotoxic macrolide, has been accomplished by employing a combination of NMR chemical shift analysis and total synthesis. The 20-membered ring of amphidinolide A was formed by a ruthenium-catalyzed alkene−alkyne coupling to forge the C15−C16 bond. Using the reported structure 1 as a starting point, a number of diastereomers of amphidinolide A were prepared. Deviations of the chemical shift of key protons in each isomer relative to the natural material were used as a guide to determine the locations of the errors in the relative stereochemistry. 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| ispartof | Journal of the American Chemical Society, 2005-10, Vol.127 (39), p.13598-13610 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Lactones - chemical synthesis Lactones - chemistry Macrolides Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Structure Organic chemistry Preparations and properties |
| title | Total Synthesis of (+)-Amphidinolide A. Structure Elucidation and Completion of the Synthesis |
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