title: Total Synthesis and Structural Revision of Clavilactone D.
abstract: A structural revision of clavilactone D, a potent inhibitor of protein tyrosine kinases, was achieved by total syntheses of two newly proposed structures. The syntheses relied on ring-opening/ring-closing metathesis, which transformed a cyclobutenecarboxylate into a γ-butenolide. The syntheses confirmed that the correct structure of clavilactone D has an amino group at C-3 instead of a hydroxy group at C-2 in the originally proposed structure.
authors.affiliation: Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Ken-Ichi
authors.identifier: http://orcid.org/0000-0001-8629-1002
authors.initials: KI
authors.lastname: Takao
authors.affiliation: Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Ryuichi
authors.initials: R
authors.lastname: Nemoto
authors.affiliation: Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Kento
authors.initials: K
authors.lastname: Mori
authors.affiliation: Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Ayumi
authors.initials: A
authors.lastname: Namba
authors.affiliation: Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Keisuke
authors.initials: K
authors.lastname: Yoshida
authors.affiliation: Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ogura
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D001487:Basidiomycota / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003503:Cyclobutanes / Q000138:chemical synthesis / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D003503:Cyclobutanes; D007783:Lactones; D047428:Protein Kinase Inhibitors; C412054:clavilactone D; C004511:butenolide; D011505:Protein-Tyrosine Kinases; D015107:4-Butyrolactone
keywords: medium-ring compounds; metathesis; natural products; structure elucidation; total synthesis