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The first total synthesis of lembehyne B

Vladimir Anatol'evich D'yakonov
Aleksey Aleksandrovich Makarov 1
Aleksey Aleksandrovich Makarov
Lilya Useinovna Dzhemileva 1
Lilya Useinovna Dzhemileva
Evgeny Nazarovich Andreev 1
Evgeny Nazarovich Andreev
Published 2017-02-27
CommunicationVolume 27, Issue 2, 122-124
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D'yakonov V. A. et al. The first total synthesis of lembehyne B // Mendeleev Communications. 2017. Vol. 27. No. 2. pp. 122-124.
GOST all authors (up to 50) Copy
D'yakonov V. A., Makarov A. A., Dzhemileva L. U., Andreev E. N., Dzhemilev U. M. The first total synthesis of lembehyne B // Mendeleev Communications. 2017. Vol. 27. No. 2. pp. 122-124.
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TY - JOUR
DO - 10.1016/j.mencom.2017.03.004
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.03.004
TI - The first total synthesis of lembehyne B
T2 - Mendeleev Communications
AU - D'yakonov, Vladimir Anatol'evich
AU - Makarov, Aleksey Aleksandrovich
AU - Dzhemileva, Lilya Useinovna
AU - Andreev, Evgeny Nazarovich
AU - Dzhemilev, Usein Memetovich
PY - 2017
DA - 2017/02/27
PB - Mendeleev Communications
SP - 122-124
IS - 2
VL - 27
ER -
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@article{2017_D'yakonov,
author = {Vladimir Anatol'evich D'yakonov and Aleksey Aleksandrovich Makarov and Lilya Useinovna Dzhemileva and Evgeny Nazarovich Andreev and Usein Memetovich Dzhemilev},
title = {The first total synthesis of lembehyne B},
journal = {Mendeleev Communications},
year = {2017},
volume = {27},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.03.004},
number = {2},
pages = {122--124},
doi = {10.1016/j.mencom.2017.03.004}
}
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D'yakonov, Vladimir Anatol'evich, et al. “The first total synthesis of lembehyne B.” Mendeleev Communications, vol. 27, no. 2, Feb. 2017, pp. 122-124. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.03.004.

Abstract

The total synthesis of lembehyne B was accomplished in five steps in 51% total yield. The cross-cyclomagnesiation of two allenic components, nonadeca-1,2-diene and pentadeca-13,14-dien-1-ol tetrahydropyranyl ether, with EtMgBr in the presence of Mg and Cp2TiCl2 catalyst (10 mol%) was used in the key step of the synthesis.

References

1.
Lembehyne A, a Novel Neuritogenic Polyacetylene, from a Marine Sponge of Haliclona sp.
2.
Total synthesis of lembehyne A, a neuritogenic spongean polyacetylene
Murakami N., Nakajima T., Kobayashi M.
Tetrahedron Letters, 2001
3.
Polyacetylenes of Marine Origin: Chemistry and Bioactivity
Zhou Z., Menna M., Cai Y., Guo Y.
Chemical Reviews, 2014
5.
Bioactive polyacetylenes in food plants of the Apiaceae family: Occurrence, bioactivity and analysis
Christensen L.P., Brandt K.
Journal of Pharmaceutical and Biomedical Analysis, 2006
6.
Chiral alkynylcarbinols from marine sponges: asymmetric synthesis and biological relevance
Listunov D., Maraval V., Chauvin R., Génisson Y.
Natural Product Reports, 2015
9.
Identification of Chiral Alkenyl- and Alkynylcarbinols as Pharmacophores for Potent Cytotoxicity
El Arfaoui D., Listunov D., Fabing I., Oukessou M., Frongia C., Lobjois V., Samson A., Ausseil F., Ben-Tama A., El Hadrami E.M., Chauvin R., Génisson Y.
ChemMedChem, 2013
10.
Cyclo- and carbomagnesiation of 1,2-dienes catalyzed by Zr complexes
Dzhemilev U.M., D'yakonov V.A., Khafizova L.O., Ibragimov A.G.
Tetrahedron, 2004
13.
Cyclomagnesation of Olefins with Ethylmagnesium Bromide in the Presence of Titanium Complexes
Dzhemilev U.M., D’yakonov V.A., Khafizova L.O., Ibragimov A.G.
Russian Journal of Organic Chemistry, 2005
14.
The facile synthesis of the 5Z,9Z-dienoic acids and their topoisomerase I inhibitory activity
D'yakonov V.A., Makarov A.A., Dzhemileva L.U., Makarova E.K., Khusnutdinova E.K., Dzhemilev U.M.
Chemical Communications, 2013
15.
nZ,(n + 4)Z-Dienoic fatty acids: a new method for the synthesis and inhibitory action on topoisomerase I and IIα
D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mulyukova A.R., Baev D.S., Khusnutdinova E.K., Tolstikova T.G., Dzhemilev U.M.
Medicinal Chemistry Research, 2015
16.
Stereoselective synthesis of 11-phenylundeca-5Z,9Z-dienoic acid and investigation of its human topoisomerase I and IIα inhibitory activity
D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mulukova A.R., Baev D.S., Khusnutdinova E.K., Tolstikova T.G., Dzhemilev U.M.
Bioorganic and Medicinal Chemistry Letters, 2015
17.
11-Phenylundeca-5Z,9Z-dienoic Acid: Stereoselective Synthesis and Dual Topoisomerase I/IIα Inhibition
D’yakonov V., Dzhemileva L., Makarov A., Mulyukova A., Baevd D., Khusnutdinova E., Tolstikova T., Dzhemilev U.
Current Cancer Drug Targets, 2015
18.
Synthesis and transformations of metallacycles. 45. Cross-cyclomagnesiation of 1,2-dienes in the synthesis of 5Z,9Z-dienoic acids, efficient inhibitors of human topoisomerase I
D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mulyukova A.R., Tuktarova R.A., Islamov I.I., Dzhemilev U.M.
Russian Chemical Bulletin, 2015
19.
Synthesis and transformations of metallacycles 41. Cyclomagnesiation of O-containing 1,2-dienes with Grignard reagents in the presence of Cp2TiCl2
20.
Short Route to the Total Synthesis of Natural Muricadienin and Investigation of Its Cytotoxic Properties
Dzhemilev U.M., D’yakonov V.A., Tuktarova R.A., Dzhemileva L.U., Ishmukhametova S.R., Yunusbaeva M.M., de Meijere A.
Journal of Natural Products, 2016
21.
The facile first total synthesis of a deuterated analog of natural muricadienin
D'yakonov V.A., Tuktarova R.A., Ishmukhametova S.R., Dzhemilev U.M.
Tetrahedron, 2016
23.
Acceleration of the Dess-Martin Oxidation by Water
Meyer S.D., Schreiber S.L.
Journal of Organic Chemistry, 1994