Synthetic studies of spiroketal enol ethers: an unexpected oxidation by Martin’s sulfurane

In an attempt to synthesize a spiroketal enol ether natural product, we found that treatment of alcohol 5 with Martin’s sulfurane did not give the anticipated olefin, but instead afforded ketone 15 through an unprecedented oxidation.

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Bibliographic Details
Published inTetrahedron letters Vol. 48; no. 13; pp. 2431 - 2434
Main Authors Wensley, Allison M., Hardy, Andrew O., Gonsalves, Kay M., Koviach, Jennifer L.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 26.03.2007
Elsevier
Subjects
Chemistry
Chemistry, Organic
Martin’s sulfurane
Physical Sciences
Propargylic oxidation
Science & Technology
Spiroketal enol ether natural products
Sulfur-based oxidation
Sulfur-based oxidation
Spiroketal enol ether natural products
Propargylic oxidation
Martin’s sulfurane
TONGHAOSU
sulfur-based oxidation
propargylic oxidation
INHIBITORS
Martin's sulfurane
spiroketal enol ether natural products
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More Information
Summary:In an attempt to synthesize a spiroketal enol ether natural product, we found that treatment of alcohol 5 with Martin’s sulfurane did not give the anticipated olefin, but instead afforded ketone 15 through an unprecedented oxidation.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.01.167