Enantioselective Synthesis of (−)-Dysiherbaine

• Published in: Organic letters Vol. 17; no. 16; pp. 3972 - 3974
• Main Authors: Do, Ha, Kang, Chang Won, Cho, Joon Hyung, Gilbertson, Scott R
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 21.08.2015; Amer Chemical Soc
• Subjects: Alanine - analogs & derivatives; Alanine - chemical synthesis; Alanine - chemistry; Alanine - pharmacology; Alkenes - chemistry; Amino Acids - chemistry; Animals; Biological Products - chemical synthesis; Biological Products - chemistry; Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis; Bridged Bicyclo Compounds, Heterocyclic - chemistry; Bridged Bicyclo Compounds, Heterocyclic - pharmacology; Chemistry; Chemistry, Organic; Marine Biology; Molecular Structure; Physical Sciences; Porifera - chemistry; Receptors, Glutamate - drug effects; Receptors, Kainic Acid - drug effects; Science & Technology; Stereoisomerism; KAINATE RECEPTORS; REARRANGEMENT; DYSIHERBAINE; AMINO-ACID; ANALOGS; SPONGE DYSIDEA-HERBACEA; NEODYSIHERBAINE-A; LEWIS-ACIDS; MARINE SPONGE
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/acs.orglett.5b01821

Dysiherbaine, a natural product isolated from the Marine sponge Dysidea herbacea, has been shown to be a selective agonist of non-NMDA type glutamate receptors, kainate receptors. An enantioselective synthesis of dysiherbaine is reported. Metathesis of the diene followed by conversion of the resulting alkene to the amino alcohol and addition of the amino acid provides the natural product. This synthesis differs from previous approaches to the molecule in that the functionality on the tetrahydropyran ring is installed late in the route.