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Indole type akuammiline from Vinca erecta: Crystal structure of 10-OAc-Akuammine
Shahobiddin Adizov (1,*) , Bakhodir Tashkhodjaev (2)
(1) Laboratory of High-Molecular Plant Substances and Physical Methods of Research, Institute of the Chemistry of Plant Substances, Academy of Sciences, 100170, Tashkent, Uzbekistan
(2) Physical methods of research, Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, 100170, Uzbekistan
(*) Corresponding Author
Received: 24 May 2019 | Revised: 21 Aug 2019 | Accepted: 24 Aug 2019 | Published: 31 Dec 2019 | Issue Date: December 2019
Single crystal X-ray diffraction has established the absolute configuration of the indole alkaloids from Vinca erecta such as akuammiline-o-acyl derivative of akuammine with a 3D stable polycyclic framework. Crystal data for C24H28N2O5: orthorhombic, space group P212121 (no. 19), a = 7.349(3) Å, b = 16.099(5) Å, c = 17.323(5) Å, V = 2049.5(12) Å3, Z = 4, T = 293(2) K, μ(CuKα) = 0.789 mm-1, Dcalc = 1.376 g/cm3, 1742 reflections measured (7.496° ≤ 2Θ ≤ 119.792°), 1742 unique (Rsigma = 0.0374) which were used in all calculations. The final R1 was 0.0608 (I > 2σ(I)) and wR2 was 0.1680 (all data). The polycyclic framework of the well-known picrinine and akuammine is compared. The ether bridges located in different positions of the framework and forming five-membered cycles do not change the conformation of the polycyclic akuammiline framework. In V. erecta alkaloids, the exomethylene fragment (C18-C19=C20-C21) of the polycyclic backbone always takes on the E-condition.
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The work was carried out according to the fundamental research projects №PZ-20170929764, №Т.4-18 and ВА-ФА-Ф6-010 S. Yunusov Institute of the Chemistry of Plant Substances Academy of Sciences Republic of Uzbekistan.
. B. Tashkhodzhaev
Indole Alkaloids from Vinca erecta, Structure and Stereochemistry
Chemistry of Natural Compounds 56(4), 587, 2020
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DOI Link: https://doi.org/10.5155/eurjchem.10.4.345-349.1898
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