Home / Publications / Synthesis of chiral 2,3-cis-fused butan-4-olides from levoglucosenone–1,3-diene Diels–Alder adducts

Synthesis of chiral 2,3-cis-fused butan-4-olides from levoglucosenone–1,3-diene Diels–Alder adducts

Anna Nikolaevna Davydova 1
Anna Nikolaevna Davydova
Alexey Aleksandrovich Pershin 1
Alexey Aleksandrovich Pershin
Bulat Tagirovich Sharipov 1
Bulat Tagirovich Sharipov
Farid Abdullovich Valeev 1
Farid Abdullovich Valeev
Published 2015-07-08
CommunicationVolume 25, Issue 4, 271-272
10
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Davydova A. N. et al. Synthesis of chiral 2,3-cis-fused butan-4-olides from levoglucosenone–1,3-diene Diels–Alder adducts // Mendeleev Communications. 2015. Vol. 25. No. 4. pp. 271-272.
GOST all authors (up to 50) Copy
Davydova A. N., Pershin A. A., Sharipov B. T., Valeev F. A. Synthesis of chiral 2,3-cis-fused butan-4-olides from levoglucosenone–1,3-diene Diels–Alder adducts // Mendeleev Communications. 2015. Vol. 25. No. 4. pp. 271-272.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2015.07.013
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.013
TI - Synthesis of chiral 2,3-cis-fused butan-4-olides from levoglucosenone–1,3-diene Diels–Alder adducts
T2 - Mendeleev Communications
AU - Davydova, Anna Nikolaevna
AU - Pershin, Alexey Aleksandrovich
AU - Sharipov, Bulat Tagirovich
AU - Valeev, Farid Abdullovich
PY - 2015
DA - 2015/07/08
PB - Mendeleev Communications
SP - 271-272
IS - 4
VL - 25
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2015_Davydova,
author = {Anna Nikolaevna Davydova and Alexey Aleksandrovich Pershin and Bulat Tagirovich Sharipov and Farid Abdullovich Valeev},
title = {Synthesis of chiral 2,3-cis-fused butan-4-olides from levoglucosenone–1,3-diene Diels–Alder adducts},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.013},
number = {4},
pages = {271--272},
doi = {10.1016/j.mencom.2015.07.013}
}
MLA
Cite this
MLA Copy
Davydova, Anna Nikolaevna, et al. “Synthesis of chiral 2,3-cis-fused butan-4-olides from levoglucosenone–1,3-diene Diels–Alder adducts.” Mendeleev Communications, vol. 25, no. 4, Jul. 2015, pp. 271-272. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.013.

Abstract

Acid-catalyzed Baeyer–Villiger oxidation of levoglucosenone–1,3-diene Diels–Alder adducts affords chiral 2,3-cis-fused (2R,3S,4S)- 4-hydroxymethylbutan-4-olides.

References

1.
A Method for Easy Preparation of Optically Pure (S)-5-Hydroxy-2-penten-4-olide and (S)-5-Hydroxypentan-4-olide
Koseki K., Ebata T., Kawakami H., Matsushita H., Naoi Y., Itoh K.
Heterocycles, 1990
2.
10.1016/j.mencom.2015.07.013_sbref0005b
Valeev
Russ. J. Org. Chem., 1993, 29, 173 Zh. Org. Khim., 1993
3.
Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)- -Pelargonolactone
Valeev F.A., Gorobets E.V., Tsypysheva I.P., Singizova G.S., Kalimullina L.K., Safarov M.G., Shitikova O.V., Miftakhov M.S.
Chemistry of Natural Compounds, 2003
4.
Conformational Analyses of Stegobinone and 1'-Epi-stegobinone
Ebata T., Koseki K., Shimazaki K., Kawakami H., Chuman T., Matsushita H., Mori K.
Heterocycles, 1990
5.
10.1016/j.mencom.2015.07.013_bib0015
Miftakhov
Russ. J. Org. Chem., 1993, 1993
7.
10.1016/j.mencom.2015.07.013_bib0025
Valeev
Russ. J. Org. Chem., 1996, 1996
8.
Cycloaddition “4 + 2” reactions of levoglucosenone
Ward D.D., Shafizadeh F.
Carbohydrate Research, 1981
9.
10.1016/j.mencom.2015.07.013_sbref0030b
Tolstikov
J. Org. Chem. USSR, 1992, 1992
11.
10.1016/j.mencom.2015.07.013_bib0035
Krow
Org. React., 1993
12.
The Baeyer-Villiger reaction: solvent effects on reaction mechanisms.
Mora-Diez N., Keller S., Alvarez-Idaboy J.R.
Organic and Biomolecular Chemistry, 2009
13.
Reactions of Peracids. V.1 The Reaction of Substituted Acetophenones with Perbenzoic Acid2
Friess S.L., Soloway A.H.
Journal of the American Chemical Society, 1951
14.
Kinetics of the Baeyer-Villiger reaction of acetophenones with permonophosphoric acid
Ogata Y., Tomizawa K., Ikeda T.
Journal of Organic Chemistry, 1978
15.
A Facile Synthesis of Bicyclo[4.2.0]octa-1,3,5-trien-3-ol
Thomas P.J., Pews R.G.
Synthetic Communications, 1991
16.
On the [4+2]-cycloaddition reaction of levoglucosenone with piperylene
Valeev F.A., Gaisina I.N., Miftakhov M.S.
Russian Chemical Bulletin, 1996
17.
Unusual regioselectivity in a Diels-Alder reaction of isoprene with levoglucosenone
Miftakhov M.S., Gaisina I.N., Valeev F.A.
Russian Chemical Bulletin, 1996