Enantiospecific synthesis of N-Boc-Adda: a linear approach |
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Authors: | Pearson C Rinehart K L Sugano M Costerison J R |
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Affiliation: | Roger Adams Laboratory, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA. |
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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. |
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