Synthesis of (-)-dysiherbaine.
[reaction: see text] The first synthesis of (-)-dysiherbaine has been accomplished using intramolecular SN2 substitutions of a carbamate anion on an epoxide and an alkoxide on a secondary mesylate to efficiently construct the bicyclic skeleton stereospecifically from xylose. A general sequence has been developed to introduce an allyl group and convert it to the alanine side chain that should be useful for the construction of dysiherbaine analogues.
Snider
B B
BB
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA. snider@brandeis.edu
Hawryluk
N A
NA
D000409:Alanine / Q000031:analogs & derivatives*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D000596:Amino Acids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D006574:Heterocyclic Compounds, 2-Ring; C121741:dysiherbaine; D000409:Alanine