title: Synthesis of the AB subunit of angelmicin B through a tandem alkoxy radical fragmentation-etherification sequence.
abstract: The synthesis of the tricyclic enone 2, corresponding to the AB subunit of the novel tyrosine kinase inhibitor angelmicin B, is described. The strategy centers on an intramolecular Diels-Alder (IMDA) reaction on triene 4 to provide the complex decalin 3, which is elaborated to 2. Other key steps are the formation of the THF ring in 2 through a tandem alkoxy radical fragmentation-etherification on the lactol derived from 3, and the synthesis of 4 via a ring-closing ene-yne metathesis (RCEYM).
authors.affiliation: Department of Chemistry, Hunter College, 695 Park Avenue, New York, New York 10065, USA.
authors.forename: Jialiang
authors.initials: J
authors.lastname: Li
authors.forename: Louis J
authors.initials: LJ
authors.lastname: Todaro
authors.forename: David R
authors.initials: DR
authors.lastname: Mootoo
mesh_terms: D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003500:Cyclization; D015394:Molecular Structure; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors*
chemical_list: D000880:Anthraquinones; C083655:angelmicin B; D011505:Protein-Tyrosine Kinases