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

Treatment 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 syringolide 2 5b is not dependent upon the presence of th...

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Bibliographic Details
Published in:Tetrahedron letters 2003-09, Vol.44 (36), p.6927-6930
Main Authors: Bennett, Simon A., Rickards, Rodney W.
Format: Article
Language:English
Subjects:
4,5,6,7-tetranorsyringolide 1
4′-deoxysyringolide 2
biomimetic
cyclisation
elicitor
syringolide 2
syringolide analogues
xylulose β-keto-esters
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Summary:Treatment 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 syringolide 2 5b is not dependent upon the presence of the 4 R-hydroxyl group. The diacyl butanolide 15 is formed simultaneously by a side reaction of the initial Knoevenagel condensation product of the ester 13c . Treatment of the 4-deoxy- d-xylulose β-ketodecanoate 13c with basic alumina affords 4′-deoxysyringolide 2 14 and the diacyl butanolide 15 .
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(03)01682-4