title: Stereoselective synthesis of the octahydronaphthalene unit of integramycin via an intramolecular Diels-Alder reaction.
abstract: [reaction: see text] The racemic cis-decalin core fragment 30 of integramycin was synthesized by a sequence involving a highly diastereoselective intramolecular Diels-Alder reaction of triene 24. A remarkable switch in stereoselectivity occurred upon changing the dienophile unit of 24 from (Z)- to (E)-geometry.
authors.affiliation: Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
authors.forename: Thomas A
authors.initials: TA
authors.lastname: Dineen
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
mesh_terms: D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009281:Naphthalenes; D013141:Spiro Compounds; C489772:integramycin