REVERSE KETAL-ACETAL REARRANGEMENT OF LEVOGLUCOSENONE AND CYCLOHEXANONE MICHAEL ADDUCTS AND THE POSSIBILITIES OF ITS USE IN THE SYNTHESIS OF NATIVE TOPOLOGY LACTONES

Authors

  • Лилия Х. Файзуллина Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054
  • Юлия А. Халилова Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054
  • Шамиль М. Салихов Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054
  • Фарид А. Валеев Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

DOI:

https://doi.org/10.1007/4934

Keywords:

аддукты Михаэля, лактоны, левоглюкозенон, кетализация

Abstract

Heating of solutions of the internal hemiketal, obtained by opening the 1,6-anhydro bridge in the Michael adduct of levoglucosenone and cyclohexanone, under reflux in THF or diglyme in the presence of NaH or Na, respectively, leads to the reduction of the hemiketal group to the ether group and oxidation of its alcohol component to the hemiacetal group. The conditions for the reverse transformation were established. Some transformations of the obtained cyclic hemiacetal have been studied. Direct methylation attempts with MeMgI in order to introduce a substituent into the 1,6-anhydro bridge were unsuccessful; therefore, the introduction of the methyl group was carried out after the oxidation of hemiacetal group to the lactone.

Authors: Liliya Kh. Faizullina*, Yuliya А. Khalilova, Shamil M. Salikhov, Farid A. Valeev

Author Biographies

Лилия Х. Файзуллина, Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

к.х.н. по специальности 02.00.03 органическая химия, доцент, старший научный сотрудник лаборатории фармакофорных циклических систем

Юлия А. Халилова, Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

к.х.н. по специальности 02.00.03 органическая химия, научный сотрудник лаборатории фармакофорных циклических систем

Шамиль М. Салихов, Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

к.х.н. по специальности 02.00.03 органическая химия,  старший научный сотрудник лаборатории физико-химических методов анализа

Фарид А. Валеев, Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

д.х.н. по специальности 02.00.03 органическая химия, профессор, главный научный сотрудник, заведующий лаборатории фармакофорных циклических систем

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Published

2019-07-23

Issue

Vol. 55 No. 7 (2019)

Section

Original Papers