Home / Publications / Stereospecific synthesis of aryltetraline lignan analogues using 1,6-bis(dipropylboryl)hexa-2,4-diene

Stereospecific synthesis of aryltetraline lignan analogues using 1,6-bis(dipropylboryl)hexa-2,4-diene

Mikhail Evguen'evich Gurskii 1
Mikhail Evguen'evich Gurskii
, 
Maxim Igorevich Zuev 1
Maxim Igorevich Zuev
, 
Artur V Eshtukov 2
Artur V Eshtukov
, 
Dmitriy Aleksandrovich Cheshkov 2
Dmitriy Aleksandrovich Cheshkov
, 
Sergey Viktorovich Baranin 1
Sergey Viktorovich Baranin
, 
Yurii Nikolaevich Bubnov 1
Yurii Nikolaevich Bubnov
10.1016/j.mencom.2021.09.033
Published 2021-09-08
Communication , Volume 31, Issue 5, 693-695
0
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Gurskii M. E. et al. Stereospecific synthesis of aryltetraline lignan analogues using 1,6-bis(dipropylboryl)hexa-2,4-diene // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 693-695.
GOST all authors (up to 50) Copy
Gurskii M. E., Zuev M. I., Eshtukov A. V., Cheshkov D. A., Baranin S. V., Bubnov Y. N. Stereospecific synthesis of aryltetraline lignan analogues using 1,6-bis(dipropylboryl)hexa-2,4-diene // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 693-695.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2021.09.033
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.033
TI - Stereospecific synthesis of aryltetraline lignan analogues using 1,6-bis(dipropylboryl)hexa-2,4-diene
T2 - Mendeleev Communications
AU - Gurskii, Mikhail Evguen'evich
AU - Zuev, Maxim Igorevich
AU - Eshtukov, Artur V
AU - Cheshkov, Dmitriy Aleksandrovich
AU - Baranin, Sergey Viktorovich
AU - Bubnov, Yurii Nikolaevich
PY - 2021
DA - 2021/09/08
PB - Mendeleev Communications
SP - 693-695
IS - 5
VL - 31
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2021_Gurskii,
author = {Mikhail Evguen'evich Gurskii and Maxim Igorevich Zuev and Artur V Eshtukov and Dmitriy Aleksandrovich Cheshkov and Sergey Viktorovich Baranin and Yurii Nikolaevich Bubnov},
title = {Stereospecific synthesis of aryltetraline lignan analogues using 1,6-bis(dipropylboryl)hexa-2,4-diene},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.033},
number = {5},
pages = {693--695},
doi = {10.1016/j.mencom.2021.09.033}
}
MLA
Cite this
MLA Copy
Gurskii, Mikhail Evguen'evich, et al. “Stereospecific synthesis of aryltetraline lignan analogues using 1,6-bis(dipropylboryl)hexa-2,4-diene.” Mendeleev Communications, vol. 31, no. 5, Sep. 2021, pp. 693-695. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.033.

Keywords

allylboration
benzylic alcohols
Friedel–Crafts reaction
lignan analogues
organoboron compounds

Abstract

A novel convenient two-stage synthesis of aryltetraline lignin analogues from aromatic aldehydes and diallyl diboron derivatives on the basis of intramolecular Friedel–Crafts reaction has been developed.

References

1.
10.1016/j.mencom.2021.09.033_b0005
Mikhailov
Bororganicheskie soedineniya v orgsnicheskom sinteze (Organoboron Compounds in Organic Synthesis), 1977
2.
10.1016/j.mencom.2021.09.033_b0010
Mikhailov
Organoboron Compounds in Organic Synthesis, 1984
3.
10.1016/j.mencom.2021.09.033_b0015
Science of Synthesis, 2004
4.
10.1016/j.mencom.2021.09.033_b0020
Pelter
Borane Reagents, 1988
5.
10.1016/j.mencom.2021.09.033_b0025
Matteson
Stereodirected Synthesis with Organoboranes, 1995
6.
Allylboranes - molecular design
Bubnov Y.N.
Pure and Applied Chemistry, 1987
7.
Allylic diboranes
Bubnov Y.N.
Pure and Applied Chemistry, 1991
8.
10.1016/j.mencom.2021.09.033_b0040
Comprehensive Heterocyclic Chemistry-II, 1996
11.
Recent advances in the boron route to asymmetric synthesis
Brown H.C., Ramachandran P.V.
Pure and Applied Chemistry, 1994
12.
10.1016/j.mencom.2021.09.033_b0060
Comprehensive Organic Synthesis, 1991
13.
Yu. N. Bubnov, M. E. Gurskii and A. V. Geiderikh, Organomet. Chem. USSR, 1989, 2, 761 (Metalloorg. Khim., 1989, 2, 1433).
15.
M. E. Gursky, A. V. Geiderikh, S. B. Golovin, A. V. Ignatenko and Yu. N. Bubnov, Russ. Chem. Bull., 1993, 42, 215 (Izv. Akad. Nauk, Ser. Khim., 1993, 236).
16.
Anfimov A.N., Erdyakov S.Y., Gurskii M.E., Ignatenko A.V., Lyssenko K.A., Bubnov Y.N.
Mendeleev Communications, 2011
17.
A. N. Anfimov, S. Yu. Erdyakov, M. E. Gurskii and Yu. N. Bubnov, Russ. Chem. Bull., Int. Ed., 2011, 60, 2336 (Izv. Akad. Nauk, Ser. Khim., 2011, 2291).
18.
The Naturally Occurring Lignans
Hearon W.M., MacGregor W.S.
Chemical Reviews, 1955
19.
The synthesis of lignans and neolignans
Ward R.S.
Chemical Society Reviews, 1982
20.
Lignans neolignans, and related compounds
Ward R.S.
Natural Product Reports, 1993
21.
Lignans, neolignans, and related compounds.
Ward R.S.
Natural Product Reports, 1999
22.
10.1016/j.mencom.2021.09.033_b0110
Ayres
Lignans: Chemical, 1990
23.
An update on lignans: natural products and synthesis.
Pan J., Chen S., Yang M., Wu J., Sinkkonen J., Zou K.
Natural Product Reports, 2009
24.
An update on bioactive plant lignans.
Saleem M., Kim H.J., Ali M.S., Lee Y.S.
Natural Product Reports, 2005
25.
Antiviral Activity of Lignans
Charlton J.L.
Journal of Natural Products, 1998
26.
ANATOLIA: NMR software for spectral analysis of total lineshape
Cheshkov D.A., Sheberstov K.F., Sinitsyn D.O., Chertkov V.A.
Magnetic Resonance in Chemistry, 2018
27.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Jr. Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and D. J. Fox, Gaussian 09, Revision A.02, Gaussian, Wallingford, CT, 2009.
28.
Stereoselective Synthesis of Tetrahydrofuran Lignans
Soorukram D., Pohmakotr M., Kuhakarn C., Reutrakul V.
Synthesis, 2018
29.
Syntheses of lignans from 2,3-diarolybutanes
Biftu T., Hazra B.G., Stevenson R., Williams J.R.
Journal of the Chemical Society Perkin Transactions 1, 1978
30.
Synthesis of Lignans. I. Nordihydroguaiaretc Acid
Perry C.W., Kalnins M.V., Deitcher K.H.
Journal of Organic Chemistry, 1972
32.
A Versatile Bis‐Allylboron Reagent for the Stereoselective Synthesis of Chiral Diols
Hetzler B.E., Volpin G., Vignoni E., Petrovic A.G., Proni G., Hu C.T., Trauner D.
Angewandte Chemie - International Edition, 2018
33.
Advances in the Synthesis of Aryltetralin Lignan Lactones
Sellars J.D., Steel P.G.
European Journal of Organic Chemistry, 2007
34.
Design, synthesis and biological evaluation of substituted (+)-SG-1 derivatives as novel anti-HIV agents
Liu X., Chen P., Li X., Ba M., Jiao X., Guo Y., Xie P.
Bioorganic and Medicinal Chemistry Letters, 2018
35.
A practical total synthesis of (+)-isogalbulin and (+)-galbulin
Li X., Jiao X., Liu X., Tian C., Dong L., Yao Y., Xie P.
Tetrahedron Letters, 2014