Enantiospecific synthesis of N-Boc-Adda: a linear approach.
[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.
Pearson
C
C
Roger Adams Laboratory, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
Rinehart
K L
KL
Sugano
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M
Costerison
J R
JR
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
D000596:Amino Acids; D001427:Bacterial Toxins; D003652:Decanoic Acids; D005563:Formic Acid Esters; C000345:t-butyloxycarbonyl group