Stereoselective total synthesis of the E-isomer of putative lucentamycin A

Title
Stereoselective total synthesis of the E-isomer of putative lucentamycin A
Authors
Selim, Khalid B이백경심태보
Keywords
E-Lucentamycin A; Olefin geometry; Reductive cyclization; Natural product; Chemical elucidation
Issue Date
2012-10
Publisher
Tetrahedron letters
Citation
VOL 53, NO 44, 5895-5898
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.
URI
http://pubs.kist.re.kr/handle/201004/43800
ISSN
00404039
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KIST Publication > Article
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