Preparation of cyclic ethers for polyether synthesis by catalytic ring-closing enyne metathesis of alkynyl ethers

Alkenyl-substituted six- and seven-membered cyclic enol ethers, which are potential building blocks for the synthesis of marine polyether natural products, can be prepared in high yield (70–97%) from alkynyl ethers by ruthenium-catalysed ring-closing enyne metathesis. The carbene-bearing ruthenium c...

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Bibliographic Details
Published inTetrahedron Vol. 58; no. 10; pp. 1973 - 1982
Main Authors Stephen Clark, J, Elustondo, Frédéric, Trevitt, Graham P, Boyall, Dean, Robertson, Jerod, Blake, Alexander J, Wilson, Claire, Stammen, Blanda
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 04.03.2002
Elsevier
Subjects
Chemistry
Chemistry, Organic
cyclic ethers
metathesis
Physical Sciences
polyether synthesis
Science & Technology
metathesis
cyclic ethers
polyether synthesis
GAMBIERIC ACIDS
ENOL ETHERS
ITERATIVE APPROACH
SUB-UNITS
OLEFIN METATHESIS
ENANTIOSELECTIVE CONSTRUCTION
POTENT ANTIFUNGAL SUBSTANCES
POLYCYCLIC ETHERS
BREVETOXIN-B
CONVERGENT SYNTHESIS
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Summary:Alkenyl-substituted six- and seven-membered cyclic enol ethers, which are potential building blocks for the synthesis of marine polyether natural products, can be prepared in high yield (70–97%) from alkynyl ethers by ruthenium-catalysed ring-closing enyne metathesis. The carbene-bearing ruthenium complex 9 is generally the most efficient catalyst for the reaction. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00053-4