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

Khalid B. Selim, Baeck Kyoung Lee, Taebo Sim

Research output: Contribution to journalArticle

4 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5895-5898
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number44
DOIs
Publication statusPublished - 2012 Oct 31

Keywords

  • Chemical elucidation
  • E-Lucentamycin A
  • Natural product
  • Olefin geometry
  • Reductive cyclization

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Stereoselective total synthesis of the E-isomer of putative lucentamycin A'. Together they form a unique fingerprint.

Cite this