Radical Cyclization of Sugar-Derived β-(Alkynyloxy)acrylates:  Synthesis of Novel Fused Ethers

Tributyltin radical mediated cyclization of carbohydrate-derived β-(alkynyloxy)acrylates leading to highly functionalized cis- and trans-fused bicyclic ethers of various ring sizes is described. The efficacy of the radical cyclization is nicely illustrated in the iterative construction of a trans-fu...

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Published inOrganic letters Vol. 2; no. 9; pp. 1275 - 1277
Main Authors Leeuwenburgh, Michiel A, Litjens, Remy E. J. N, Codée, Jeroen D. C, Overkleeft, Herman S, van der Marel, Gijsbert A, van Boom, Jacques H
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.05.2000
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXACYCLE SYNTHESIS
RING-CLOSING METATHESIS
CIGUATOXIN
STRATEGY
CONSTRUCTION
PTYCHODISCUS-BREVIS
CARBOHYDRATE-DERIVATIVES
BETA-ALKOXYACRYLATES
GAMBIERDISCUS-TOXICUS
BREVETOXIN-B
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Summary:Tributyltin radical mediated cyclization of carbohydrate-derived β-(alkynyloxy)acrylates leading to highly functionalized cis- and trans-fused bicyclic ethers of various ring sizes is described. The efficacy of the radical cyclization is nicely illustrated in the iterative construction of a trans-fused tricyclic tetrahydropyran.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0000408