title: Enantiospecific synthesis of N-Boc-Adda: a linear approach.
abstract: [structure: see text] Synthesis of the unusual amino acid (2S,3S,8S, 9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoic acid (Adda), a unit of numerous cyanobacterial toxins, is described. Construction of the target molecule was achieved in 13 steps with an overall yield of 40%. The work is highlighted by a novel one-pot transformation from isoxazolidin-5-one intermediate 6 to the final product, a step that can also be used to form beta-amino acids.
authors.affiliation: Roger Adams Laboratory, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
authors.forename: C
authors.initials: C
authors.lastname: Pearson
authors.forename: K L
authors.initials: KL
authors.lastname: Rinehart
authors.forename: M
authors.initials: M
authors.lastname: Sugano
authors.forename: J R
authors.initials: JR
authors.lastname: Costerison
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis*; D001427:Bacterial Toxins / Q000737:chemistry; D000458:Cyanobacteria / Q000737:chemistry; D003652:Decanoic Acids / Q000737:chemistry*; D005563:Formic Acid Esters / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001427:Bacterial Toxins; D003652:Decanoic Acids; D005563:Formic Acid Esters; C000345:t-butyloxycarbonyl group