title: Total synthesis of (±)-bisabosqual A.
abstract: The synthesis of the novel squalene synthase inhibitor, bisabosqual A, was completed in 14 steps (longest linear sequence) from commercially available starting materials. The doubly convergent route employs a tandem 5-exo, 6-exo radical cyclization as the key step. This reaction assembles the fully functionalized tetracyclic core and introduces three stereogenic centers. Other effective transformations are the regioselective deoxygenation of an advanced enone intermediate and the chemo- and diastereoselective addition of trimethylaluminum to a ketone in the presence of esters.
authors.affiliation: Department of Chemistry, Stony Brook University, Stony Brook, New York 11794, USA.
authors.forename: Christopher W
authors.initials: CW
authors.lastname: am Ende
authors.forename: Zhou
authors.initials: Z
authors.lastname: Zhou
authors.forename: Kathlyn A
authors.initials: KA
authors.lastname: Parker
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013186:Farnesyl-Diphosphate Farnesyltransferase / Q000037:antagonists & inhibitors*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular
chemical_list: D004791:Enzyme Inhibitors; D006576:Heterocyclic Compounds, 4 or More Rings; C581734:bisabosqual A; D013186:Farnesyl-Diphosphate Farnesyltransferase