Chemistry and Structure of Diterpene Compounds of the Kaurane Series: VII. Chiral Complexes of Isosteviol with Aromatic Compounds

(4,8,13)-13-Methyl-16-oxo-17-norkaurane-18-carboxylic acid (isosteviol) forms with aniline, dimethylaniline, and toluene individual 2:1 molecular complexes whose crystals are isostructural. According to X-ray diffraction data, the supramolecular crystal structure of these complexes is formed by chiral double helices with a 4₃ screw axis, consisting of isosteviol molecules. The strands of the helices are linked together by intermolecular hydrogen bonds involving the carboxy and carbonyl groups of two isosteviol molecules of neighboring helices. In their turn, the two hydrogen-bonded isosteviol molecules form head-to-tail pseudocage dimers. The aromatic guests occupy fairly large cavities between the strands of isosteviol helices.     

Study of the rotational isomerism about the C-O bond in six-membered secondary-tertiary diols

We have determined the spectroscopic characteristics, the dipole moments, and the Kerr constants of the stereoisomers of the secondary-tertiary diols of the cyclohexane and bicyclo [4.1.0]pentane series: 3,4-dihydroxy-3-carane (I), 3,4-dihydroxy-3-methylnorcarane (II), 3,4-dihydroxy-3-methylnorcarane (III), 4, 5-dihydroxy-3-methylcyclohexene (IV), 3,4-dihydroxy-3-carane (V), 3,4-dihydroxy-3-methylnorcarane (VI), 3, 4-dihydroxy-3-carane (VII), and 3,4-dihydroxy-4-methyl-3-carane (VIII). It was found that the cis diols are more polar than their trans isomers. It was shown by electrical and electrooptical methods that rotamers with a gauche orientation with respect to the tertiary C-O are stable relative to those containing the diol at the ordinary C-C bond of the ring.Deceased.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 619–625, March, 1991.     

Reaction of 3α-Hydroxy-4β-Chlorocarane with POCl3

Conclusions The action of POCl₃ on 3-hydroxy-4-chlorocarane gives products of cleavage, substitution, and allyl rearrangement with retention of the carane skeleton of the starting molecule.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 919–922, April, 1985.     

Rotational isomerism relative to C-O bonds in stereoisomeric cyclic trans-methoxy alcohols

Conclusions The dipole moments and Kerr constants of monomethyl ethers of trans-3,4-diols of the bicyclo[4.1.0]heptane series and cyclohexane were determined. Based on the set of data from physical methods, a conclusion was drawn concerning the conformational equilibrium of the compounds and the rotational states relative to the C-O bonds.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1768–1772, August, 1988.     

Chemistry and Structure of Diterpene Derivatives of the Kaurane Series: V. Isosteviol Anhydrides

(4,8,13)-13-Methyl-16-oxo-17-norkaurane-18-carboxylic acid (isosteviol) anhydride is synthesized, which is a first representative of bisditerpene compounds of the kaurane series. The structures of the anhydride and isosteviol chloride were studies by X-ray diffraction and quantum chemistry (AM1).     

Stereochemistry of epoxidation of 4α-chloro-3(10)-carene

Conclusions Epoxidation of 4-chloro-3(10)-carene with peracetic acid gives a mixture of stereoisomeric 4-chloro-3,10-epoxycaranes with preferential formation of the cis isomer.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 832–835, April, 1979.     

Chemistry and Structure of Diterpenoids: X. Isosteviol Amides

Acylation of amino alcohols with isosteviol chloride, depending on the reactant ratio, leads to formation of either bis-isosteviol derivatives or N-acylation products. Reactions of aromatic diamines with 2 equiv of isosteviol chloride give the corresponding N,N′-bis(isostevioyl) derivatives.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 2, 2005, pp. 276–281.Original Russian Text Copyright © 2005 by Al’fonsov, Kataev, Strobykina, Korochkina, Kovylyaeva, Bakaleinik, Beskrovnyi, Gubaidullin, Litvinov, Musin.For communication IX, see [1].