Stereoselective total synthesis of the E-isomer of putative lucentamycin A |
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Authors: | Khalid B SelimBaeck Kyoung Lee Taebo Sim |
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Institution: | Future Convergence Research Division, Korea Institute of Science and Technology, PO Box 131, Cheongryang, Seoul 130-650, Republic of Korea |
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Abstract: | A synthesis of the E-isomer of the proposed structure of the novel tripeptide, lucentamycin A, was performed in an attempt to define the correct stereochemistry of this natural product. The synthetic route developed employs a stereoselective Rh-catalyzed reductive cyclization process to generate the key pyrrolidine residue in the target and a stereospecific inversion of the Z-olefin geometry to form desired E-isomer. Subsequent amide coupling reactions afforded the desired E-isomer of putative lucentamycin A. A comparison of the NMR data of synthetic E-1a with that of the naturally occurring lucentamycin A demonstrated that they are not identical substances and the E-1a was found to display no anti-proliferative activity on the colon cancer cell line HCT-116 in contrast to natural lucentamycin A. |
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Keywords: | E-Lucentamycin A Olefin geometry Reductive cyclization Natural product Chemical elucidation |
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