Factors controlling the biomimetic triple cyclisation of xylulose β-keto-esters to syringolides. Part 1: Synthesis of 4-deoxysyringolide 2.

Bennett, SimonRickards, Rodney2015-12-132015-12-130040-4039http://hdl.handle.net/1885/87879Treatment of the 4-deoxy-D-xylulose β-ketodecanoate 13c with basic alumina affords 4′-deoxysyringolide 2 14 as a single stereoisomer, indicating that the course of the biomimetic triple cyclisation of the corresponding D-xylulose ester 3b to syringolidKeywords: amide; syringolide; unclassified drug; xylulose; article; biomimetics; Knoevenagel condensation; Michael addition; stereoisomerism; synthesis 4'-deoxysyringolide 2; 4,5,6,7-tetranorsyringolide 1; Biomimetic; Cyclisation; Elicitor; Syringolide 2; Syringolide analogues; Xylulose ß-keto-estersFactors controlling the biomimetic triple cyclisation of xylulose β-keto-esters to syringolides. Part 1: Synthesis of 4-deoxysyringolide 2.200310.1016/S0040-4039(03)01682-42015-12-12