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

Simon A. Bennett; Rodney W. Rickards

doi:10.1016/S0040-4039(03)01682-4

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

Simon A. Bennett
, Rodney W. Rickards^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

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 syringolide 2 5b is not dependent upon the presence of the 4R-hydroxyl group. The diacyl butanolide 15 is formed simultaneously by a side reaction of the initial Knoevenagel condensation product of the ester 13c.

Original language	English
Pages (from-to)	6927-6930
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	36
DOIs	https://doi.org/10.1016/S0040-4039(03)01682-4
Publication status	Published - 1 Sept 2003

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

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 syringolide 2 5b is not dependent upon the presence of the 4R-hydroxyl group. The diacyl butanolide 15 is formed simultaneously by a side reaction of the initial Knoevenagel condensation product of the ester 13c.",

keywords = "4,5,6,7-tetranorsyringolide 1, 4′-deoxysyringolide 2, Biomimetic, Cyclisation, Elicitor, Syringolide 2, Syringolide analogues, Xylulose β-keto-esters",

author = "Bennett, \{Simon A.\} and Rickards, \{Rodney W.\}",

year = "2003",

month = sep,

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doi = "10.1016/S0040-4039(03)01682-4",

language = "English",

volume = "44",

pages = "6927--6930",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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number = "36",

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TY - JOUR

T1 - Factors controlling the biomimetic triple cyclisation of xylulose β-keto-esters to syringolides. Part 1

T2 - Synthesis of 4′-deoxysyringolide 2

AU - Bennett, Simon A.

AU - Rickards, Rodney W.

PY - 2003/9/1

Y1 - 2003/9/1

N2 - 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 4R-hydroxyl group. The diacyl butanolide 15 is formed simultaneously by a side reaction of the initial Knoevenagel condensation product of the ester 13c.

AB - 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 4R-hydroxyl group. The diacyl butanolide 15 is formed simultaneously by a side reaction of the initial Knoevenagel condensation product of the ester 13c.

KW - 4,5,6,7-tetranorsyringolide 1

KW - 4′-deoxysyringolide 2

KW - Biomimetic

KW - Cyclisation

KW - Elicitor

KW - Syringolide 2

KW - Syringolide analogues

KW - Xylulose β-keto-esters

UR - https://www.scopus.com/pages/publications/0042659716

U2 - 10.1016/S0040-4039(03)01682-4

DO - 10.1016/S0040-4039(03)01682-4

M3 - Article

SN - 0040-4039

VL - 44

SP - 6927

EP - 6930

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

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

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