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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.[1]


  1. Synthesis of (-)-dysiherbaine. Snider, B.B., Hawryluk, N.A. Org. Lett. (2000) [Pubmed]
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