title: Stereoselective synthesis of deuterium-labeled (2S)-cyclohexenyl alanines, biosynthetic intermediates of cinnabaramide.
abstract: Dideuterated β-cyclohexenylalanines, proposed biosynthetic intermediates of the cinnabaramides, can be obtained from chiral alkynols via a sequence of Irland-Claisen rearrangement, ring closing metathesis, and radical decarboxylation. Feeding experiments indicate that both (2S)-β-cyclohexenylalanines can be incorporated into cinnabaramide, while the configuration at the cyclohexenyl ring does not restrict biosynthetic processing.
authors.affiliation: Saarland University, Institute of Organic Chemistry, Campus, Bldg. C4.2, D-66123 Saarbruecken, Germany.
authors.forename: Philipp
authors.initials: P
authors.lastname: Barbie
authors.forename: Liujie
authors.initials: L
authors.lastname: Huo
authors.forename: Rolf
authors.initials: R
authors.lastname: Müller
authors.forename: Uli
authors.initials: U
authors.lastname: Kazmaier
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D001224:Aspartic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D053138:Cyclohexenes / Q000138:chemical synthesis* / Q000737:chemistry; D003903:Deuterium / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D053138:Cyclohexenes; D007783:Lactones; C521217:cinnabaramide A; D001224:Aspartic Acid; D003903:Deuterium; D000409:Alanine