title: Adaptation of a small-molecule hydrogen-bond donor catalyst to an enantioselective hetero-Diels-Alder reaction hypothesized for brevianamide biosynthesis.
abstract: Chiral diamine-derived hydrogen-bond donors were evaluated for their ability to effect stereocontrol in an intramolecular hetero-Diels-Alder (HDA) reaction hypothesized in the biosynthesis of brevianamides A and B. Collectively, these results provide proof of principle that small-molecule hydrogen-bond catalysis, if even based on a hypothetical biosynthesis construct, holds significant potential within enantioselective natural product synthesis.
authors.affiliation: Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University , Nashville, Tennessee 37235, United States.
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Sprague
authors.forename: Benjamin M
authors.initials: BM
authors.lastname: Nugent
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Yoder
authors.forename: Brandon A
authors.initials: BA
authors.lastname: Vara
authors.forename: Jeffrey N
authors.initials: JN
authors.lastname: Johnston
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D006860:Hydrogen Bonding; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D010879:Piperazines; D013141:Spiro Compounds; C006794:brevianamide A; C116214:brevianamide B