title: Total synthesis of (±)-streptonigrin: de novo construction of a pentasubstituted pyridine using ring-closing metathesis.
abstract: The synthesis of the potent antitumor agent (±)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. Timothy.donohoe@chem.ox.ac.uk
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Donohoe
authors.forename: Christopher R
authors.initials: CR
authors.lastname: Jones
authors.forename: Luiz C A
authors.initials: LC
authors.lastname: Barbosa
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism; D013308:Streptonigrin / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D011725:Pyridines; D013308:Streptonigrin; C023666:pyridine