title: Progress toward the total synthesis of lucentamycin A: total synthesis and biological evaluation of 8-epi-lucentamycin A.
abstract: 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.
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37232, USA.
authors.forename: R Nathan
authors.initials: RN
authors.lastname: Daniels
authors.forename: Bruce J
authors.initials: BJ
authors.lastname: Melancon
authors.forename: Emily A
authors.initials: EA
authors.lastname: Wang
authors.forename: Brenda C
authors.initials: BC
authors.lastname: Crews
authors.forename: Lawrence J
authors.initials: LJ
authors.lastname: Marnett
authors.forename: Gary A
authors.initials: GA
authors.lastname: Sulikowski
authors.forename: Craig W
authors.initials: CW
authors.lastname: Lindsley
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D008968:Molecular Conformation; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D009842:Oligopeptides; C523222:lucentamycin A