Snider B B, Hawryluk N A
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Org Lett. 2000 Mar 9;2(5):635-8. doi: 10.1021/ol991393d.
[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.
