title: Total synthesis and structural revision of lucentamycin A.
abstract: Lucentamycin A is a marine-derived peptide natural product harboring a unique 4-ethylidene-3-methylproline (Emp) subunit. The proposed structure of lucentamycin A and the core Emp residue have recently been called into question through synthesis. Here, we report the first total synthesis of lucentamycin A, which confirms that the ethylidene substituent in Emp bears an E geometry, in contrast to the originally assigned Z configuration. Synthesis of the desired (E)-Emp subunit required the implementation of a novel strategy starting from Garner's aldehyde.
authors.affiliation: Drug Discovery Department, H. Lee Moffitt Cancer Center and Research Institute, Tampa, Florida 33612, United States.
authors.forename: Sujeewa
authors.initials: S
authors.lastname: Ranatunga
authors.forename: Chih-Hang Anthony
authors.initials: CH
authors.lastname: Tang
authors.forename: Chih-Chi Andrew
authors.initials: CC
authors.lastname: Hu
authors.forename: Juan R
authors.initials: JR
authors.lastname: Del Valle
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D009842:Oligopeptides; C523222:lucentamycin A; D011392:Proline