Synthesis of santonin related compounds

(±)-1-Nordesmotroposantonin ( 2 ), a thermolysis product of santonin, and its isomer, α-(1,2,3,4-tetrahydro-1,7-dihydroxy-α,6-dimethyl-2-naphthalene)acetic acid γ-lactone ( 3 ) were synthesized from 4-(4-methoxy-3-ethylphenyl)butanoic acid.     

Olivomycin and related antibiotics

Conclusions On the basis of its chemical properties and spectral characteristics, structure I has been established for the aglycone of the olivomycin antibiotics, olivin.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 4, pp. 304–316, 1969For part XIII, see [1], and for a preliminary communication, see [2]. The subject matter of the present paper was presented in part at the International Congress on Antibiotics (Prague, 1964), and at the IX-th Mendeleev Conference on General and Applied Chemistry (Kiev, 1965).     

Olivomycin and related antibiotics

Summary 1. From the culture fluid of the ray fungusActinomyces olivoreticuli four individual antibiotics, olivomycins A, B, C, and D have been isolated.2. The acid degradation of olivomycins A, B, C, and D has been carried out with the formation of the aglycone olivin and the carbohydrates olivomycose, olivomose, olivose, oliose, and (or) their derivatives.3. The qualitative and quantitative monomeric composition of olivomycins A, B, C, and D has been elucidated and their empirical formulas have been established.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 5, pp. 331–339, 1967For previous communications, see [1]; for Communication IX, see [2].     

Olivomycin and related antibiotics

Conclusions It has been shown that the five monosaccharide residues forming the carbohydrate moiety of the antibiotic olivomycin A form two unbranched chains attached to the hydroxyls in positions 2 and 6 of the aglycone and terminated by isobutyrylolivomycose and olivomose.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 6, pp. 561–566, 1969For a preliminary communication, see [1], and for part XVI, see [2].     

Hydroacridines and related compounds

One hydrogen atom is replaced by lithium in the reaction of 1,2,3,4-tetrahydroacridine and sym-octahydroacridine with phenyllithium; effective replacement of a second hydrogen atom by lithium becomes possible after replacement of the first lithium by an alkyl group. This makes it possible to achieve step-wise alkylation.See [1] for communication VIII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 673–675, May, 1972.     

Gibberellins and related compounds

Conclusions A study was made of the photochemical aromatization of the 2-keto derivative of gibberellic acid in various solvents. Unusual fragmentation of the B ring, with the formation of the seco-structure, was observed when the reaction was run in benzyl alcohol.Deceased.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2037–2040, September, 1971.     

Deoxycelluloses and related structures

The syntheses of various deoxycelluloses and related structures (cellulosenes and anhydrocelluloses) from the mid‐1920s to the present are critically reviewed. General synthetic strategies to prepare deoxycelluloses include nucleophilic displacement of good leaving groups. Distinctions are made between reaction of cellulosics under homogeneous and heterogeneous conditions. Recent advances in the preparation of halodeoxycelluloses have led to high degree of substitution fluorodeoxycelluloses and bromodeoxycelluloses. Applications for the deoxycelluloses are numerous and characterized by biological, chemical or physical end uses.     

Benzimidazoles and related heterocycles

3-Aryl-1’H-spiro[2-pyrazoline-5,2’-quinoxalin]-3’(4’H)-ones, easily available by the reaction of 3-(2-aryl-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-ones with hydrazine hydrate (and phenylhydrazine), in boiling acetic acid undergo new acid-catalyzed rearrangement with the contraction of pyrazine ring of the quinoxaline system to form 2-(pyrazol-3-yl)benzimidazoles. Possible mechanisms of this rearrangement are considered.     

Hydroacridines and related compounds

The stereochemistry of the hydride reduction of N-substituted 4a-cyano-, 4a,10a-dicyano-, and 4a,10a-peroxy-9-phenylperhydroacridines was studied. The configuration of a series of isomeric N-substituted 9-phenylperhydroacridines was established.See [1] for communication XIV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 508–512, April, 1977.     

Benzoxazines and related compounds

Interconversion of 2-alkyl-4,4-diethyl-4H-1,3-benzoxazines and N-acyl-,-diethyl-o-hydroxybenzylamines was accomplished, and it is shown that cupric ion catalyzes these reactions.See [1] for Communication II.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1465–1466, November, 1970.     

Hydroacridines and related compounds

Some N-aryldecahydroacridines reduce N=N, C=N, C=O, NO₂, and acridine groups in acidic media. In neutral media, N-aryldecahydroacridines are oxidized by caloranil and polyhaloalkanes.     

Allylcyclooctatetraenetitanium and related complexes

The compounds (C₈H₈-h₈) (R-h₃)Ti with R = allyl, 1- and 2-methylallyl have been prepared by treatment of [(C₈H₈-h₈)TiCl-THF]₂ with RMgX (X = Cl, Br) in ether and the compounds (C₈H₈-h₈) (R-h₃)Ti-THF from the same reaction in THF. The green, paramagnetic compounds are sensitive to air and water. They decompose slowly at room temperature, but they can be stored at ?30° without change. The IR spectra indicate that a C₈H₈-h₈ and an allylic-h₃ group are present in the molecule. Analogous compounds of vanadium could not be obtained.     

Benzoxazines and related compounds

The reaction of 2-mercapto(and benzylthio)-α,α-dialkylbenzyl alcohols with nitriles under the influence of acids serves as a method for the synthesis of 2,4,4-trisubstituted 4H-1,3-benzothiazines.