Reversible intramolecular Dieckmann-type condensation of 2-(2-hydroxymethyl-5,5,6-trimethoxytetrahydropyran-3-ylcarbonyl)-cyclopentanone: an alternative access to medium-sized lactones

[Display omitted] Levoglucosenone-derived 2-[(2S,3S,6S)-2-hydroxymethyl-5,5,6-trimethoxytetrahydro-2H-pyran-3-ylcarbonyl]cyclo-pentanone upon boiling in benzene in the presence of NaH undergoes the retro-Dieckmann-type reaction to afford 10-membered lactone, while storing this reaction mixture at ro...

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Published in:Mendeleev communications 2019-01, Vol.29 (1), p.64-66
Main Authors: Faizullina, Liliya Kh, Galimova, Yuliya S., Ovchinnikov, Mikhail Yu, Salikhov, Shamil M., Khursan, Sergey L., Valeev, Farid A.
Format: Article
Language:English
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Summary:[Display omitted] Levoglucosenone-derived 2-[(2S,3S,6S)-2-hydroxymethyl-5,5,6-trimethoxytetrahydro-2H-pyran-3-ylcarbonyl]cyclo-pentanone upon boiling in benzene in the presence of NaH undergoes the retro-Dieckmann-type reaction to afford 10-membered lactone, while storing this reaction mixture at room temperature brings about the starting cyclopentanone derivative. Several structurally analogous compounds were examined in respect of similar transformations.
ISSN:0959-9436
DOI:10.1016/j.mencom.2019.01.021