Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 21, Pages 10357-10365Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01339
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- Deutsche Bundesumweltstiftung (KONAROM) [AZ 26920]
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An atom-economic reaction sequence to 6-substituted 2-pyrones was developed starting from furfuryl alcohol, a renewable resource made from bran or bagasse, and aldehydes, utilizing a thermal rearrangement of cyclopentadienone epoxides as key step. Derivatives bearing a hydroxyalkyl side chain could be enzymatically resolved, providing access to enantiomerically pure 2-pyrones, or converted to alkenyl-substituted 2-pyrones such as naturally occurring sibirinone, (E)-6-(pent-1-en-1-yl)-2H-pyran-2-one, and (E)-6-(hept-l-en-l-yl)-2H-pyran-2-one.
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