Stereoselective total synthesis of the E-isomer of putative lucentamycin A
- Stereoselective total synthesis of the E-isomer of putative lucentamycin A
- Selim, Khalid B; 이백경; 심태보
- E-Lucentamycin A; Olefin geometry; Reductive cyclization; Natural product; Chemical elucidation
- Issue Date
- Tetrahedron letters
- VOL 53, NO 44, 5895-5898
- 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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