title: Synthesis of the ring system of phomactin D using a Suzuki macrocyclization.
abstract: [reaction: see text]The ring system of phomactin D was synthesized in racemic form in an efficient manner from 2,3-dimethylcyclohexanone. Notable transformations include (1) an alkylation of the enolate of a vinylogous thiolester to install a quaternary stereocenter, (2) a conjugate addition of cyanide to an alpha,beta-unsaturated aldehyde, (3) the formation of a Weinreb amide directly from a cyanohydrin, and (4) an intramolecular Pd-mediated Suzuki coupling of a B-alkyl-9-BBN derivative and a vinyl iodide to form the macrocyclic ring.
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado, Boulder 80309-0215, USA.
authors.forename: N C
authors.initials: NC
authors.lastname: Kallan
authors.forename: R L
authors.initials: RL
authors.lastname: Halcomb
mesh_terms: D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D010972:Platelet Activating Factor / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D007202:Indicators and Reagents; D010972:Platelet Activating Factor; C103093:phomactin D