Progress toward the total synthesis of lucentamycin A: total synthesis and biological evaluation of 8-epi-lucentamycin A.

Daniels RN, Melancon BJ, Wang EA, Crews BC, Marnett LJ, Sulikowski GA, Lindsley CW
J Org Chem. 2009 74 (22): 8852-5

PMID: 19908916 · DOI:10.1021/jo902115s

Synthetic efforts toward the cytotoxic peptides lucentamycins A-D are described that resulted in the total synthesis and biological evaluation of 8-epi-lucentamycin A in 15 steps with 2.2% overall yield. The key epi-nonproteogenic 3-methyl-4-ethylideneproline was synthesized via a titanium-mediated cycloisomerization reaction.

MeSH Terms (9)

Antineoplastic Agents Cell Line, Tumor Cell Proliferation Drug Screening Assays, Antitumor Humans Inhibitory Concentration 50 Molecular Conformation Oligopeptides Stereoisomerism

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