title: Diverging stereochemical pathways in an intramolecular Diels-Alder reaction determined by dienophile structure.
abstract: [reaction: see text] Intramolecular Diels-Alder cycloaddition of tolylsulfonyl alkynone 5a and vinyl ketone 19 led to single isomers with opposite diastereoselectivity. Decalin 20 incorporates the correct C(9)-C(11) stereochemical array for a projected synthesis of HMP-Y1 (1).
authors.affiliation: Department of Chemistry, Texas A&M University, College Station, Texas 77842, USA.
authors.forename: Kwangho
authors.initials: K
authors.lastname: Kim
authors.forename: Umar S M
authors.initials: US
authors.lastname: Maharoof
authors.forename: Jessica
authors.initials: J
authors.lastname: Raushel
authors.forename: Gary A
authors.initials: GA
authors.lastname: Sulikowski
mesh_terms: D015394:Molecular Structure; D013237:Stereoisomerism