title: Investigations into an anionic oxy-cope/transannular conjugate addition approach to 7,20-diisocyanoadociane.
abstract: An anionic oxy-Cope/transannular conjugate addition approach to the potent antimalarial 7,20-diisocyanoadociane is presented. The unexpected formation of undesired diastereomers in the key reaction led to the structural reassignment of previous products of this type of cascade and a reevaluation of the reversibility of the transannular ring closure. During efforts to coax the reaction toward the desired product, a transannular ene reaction provided tricyclic compounds relevant to the kempane diterpenoids.
authors.affiliation: Department of Chemistry, 1102 Natural Sciences II, University of California , Irvine, California 92697-2025, United States.
authors.forename: Philipp C
authors.initials: PC
authors.lastname: Roosen
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Vanderwal
mesh_terms: D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011721:Pyrenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000962:Antimalarials; D004224:Diterpenes; D009570:Nitriles; D011721:Pyrenes; C424431:diisocyanoadociane