title: Total synthesis and biological evaluation of ustiloxin natural products and two analogs.
abstract: Synthetic investigations of ustiloxin natural products are described. The first total synthesis of ustiloxin F was completed in 15 steps via ethynyl aziridine ring-opening by a phenol derivative. The results of biological tests of synthetic ustiloxins D and F, and two analogs, O-Me-ustiloxin D and 6-Ile-ustiloxin, demonstrated that the free hydroxyl group ortho to the ether linkage is critical for activity and variations at the Val/Ala site produce changes in the biological activity suggesting the need for further perturbations at this site to more extensively study the tubulin binding.
authors.affiliation: Department of Chemistry, University of Pennsylvania, 231 S. 34th Street, Philadelphia, PA 19104, USA.
authors.forename: Pixu
authors.initials: P
authors.lastname: Li
authors.forename: Cory D
authors.initials: CD
authors.lastname: Evans
authors.forename: Erin M
authors.initials: EM
authors.lastname: Forbeck
authors.forename: Haengsoon
authors.initials: H
authors.lastname: Park
authors.forename: Ruoli
authors.initials: R
authors.lastname: Bai
authors.forename: Ernest
authors.initials: E
authors.lastname: Hamel
authors.forename: M M
authors.initials: MM
authors.lastname: Joullié
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D009183:Mycotoxins / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014404:Tubulin / Q000378:metabolism; D009842:Oligopeptides
chemical_list: D001688:Biological Products; D009183:Mycotoxins; D010456:Peptides, Cyclic; D014404:Tubulin; C112875:ustiloxin F; C089079:ustiloxin D; C035753:phomopsin; D009842:Oligopeptides