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.
Citation:
V. A. D'yakonov, A. A. Makarov, L. U. Dzhemileva, E. N. Andreev, U. M. Dzhemilev, “The first total synthesis of lembehyne B”, Mendeleev Commun., 27:2 (2017), 122–124
Linking options:
https://www.mathnet.ru/eng/mendc1916
https://www.mathnet.ru/eng/mendc/v27/i2/p122
This publication is cited in the following 13 articles:
I. I. Islamov, A. A. Makarov, E. Kh. Makarova, A. V. Yusupova, V. A. D'yakonov, U. M. Dzhemilev, “Synthesis of macrocyclic and linear compounds with 1Z,5Z-diene and alkynylcarbinol fragments based on (5Z,9Z)-tetradeca-5,9-diene-1,14-diol”, Russ Chem Bull, 72:4 (2023), 925
U. M. Dzhemilev, L. U. Dzhemileva, V. A. D'yakonov, “Metallacomplex catalysis in the synthesis of regular isoprenoids”, Russ Chem Bull, 72:2 (2023), 404
Alexey A. Makarov, Lilya U. Dzhemileva, Elina Kh. Makarova, Usein M. Dzhemilev, The 26th International Electronic Conference on Synthetic Organic Chemistry, 2022, 19
Elina Kh. Makarova, Lilya U. Dzhemileva, Alexey A. Makarov, Usein M. Dzhemilev, The 26th International Electronic Conference on Synthetic Organic Chemistry, 2022, 61
Alexey A. Makarov, Elina Kh. Makarova, Lilya U. Dzhemileva, Usein M. Dzhemilev, The 25th International Electronic Conference on Synthetic Organic Chemistry, 2021, 29
Alexey A. Makarov, Elina Kh. Makarova, Lilya U. Dzhemileva, Usein M. Dzhemilev, The 25th International Electronic Conference on Synthetic Organic Chemistry, 2021, 30
Vladimir A. D'yakonov, Lilya U. Dzhemileva, Usein M. Dzhemilev, “Natural compounds with bis-methylene-interrupted Z-double bonds: plant sources, strategies of total synthesis, biological activity, and perspectives”, Phytochem Rev, 20:1 (2021), 325
Lilya U. Dzhemileva, Alexey A. Makarov, Evgeny N. Andreev, Elina Kh. Makarova, Milyausha M. Yunusbaeva, Vladimir A. D'yakonov, Usein M. Dzhemilev, “New 1,3-Diynoic Derivatives of Natural Lembehyne B: Stereoselective Synthesis, Anticancer, and Neuritogenic Activity”, ACS Omega, 5:4 (2020), 1974
Novriyandi Hanif, Anggia Murni, Chiaki Tanaka, Junichi Tanaka, “Marine Natural Products from Indonesian Waters”, Marine Drugs, 17:6 (2019), 364
D. Liang, Yu. Wang, “The first synthesis of 7-prenylisatin”, Mendeleev Commun., 29:2 (2019), 172–173
V. A. D'yakonov, I. I. Islamov, E. M. Khusainova, U. M. Dzhemilev, “Original catalytic synthesis of macrodiolides containing a 1Z,5Z-diene moiety”, Mendeleev Commun., 28:5 (2018), 503–504
Vladimir A. D'yakonov, Ilgiz I. Islamov, Aleksey A. Makarov, Usein M. Dzhemilev, “Ti-catalyzed cross-cyclomagnesiation of 1,2-dienes in the stereoselective synthesis of insect pheromones”, Tetrahedron Letters, 58:18 (2017), 1755
Contact us: