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

Date

Authors

Bennett, Simon

Rickards, Rodney

Publisher

Elsevier

Abstract

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 syringolid

Keywords

Keywords: 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-esters

URI

http://hdl.handle.net/1885/87879

Collections

ANU Research Publications

Source

Tetrahedron Letters

Type

Journal article

DOI

10.1016/S0040-4039(03)01682-4