1686-62-0Relevant articles and documents
Synthetic Transformations of Higher Terpenoids. 36.* Synthesis of 13-(Oxazol-5-Yl)-15,16-Bisnorisopimaranes
Gromova,Kharitonov, Yu. V.,Rybalova,Shul’ts
, p. 293 - 300 (2018/04/17)
The conditions for oxidizing methyl isopimarate to the 15-oxo-15,16-dihydroisopimarate were studied. The latter was used for one-pot syntheses of 13-(oxazol-5-yl)-15,16-bisnorisopimarates that included formation of the 16-oxoaldehyde isopimarate and its c
A 7 - carbonyl - 8, 15 - ISO pimaric acid methyl ester preparation method (by machine translation)
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Paragraph 0038, (2017/06/29)
The invention discloses a 7 - carbonyl - 8, 15 - ISO pimaric acid methyl ester preparation method, the specific method is: will be different pimaric acid methyl ester dissolved in a solvent to prepare the solution, wet film maker tinplate sheet colored uniform liquid film, in order to ma Kou iron sheet for the reactor, under UV irradiation of light air oxidation reaction. After the leaching reaction solvent for coating, will be of the showering liquid evaporate the solvent to obtain the oxidation product. Oxidation product after the dissolution of the solvent used, utilizing preparative thin layer chromatography separation and purification to obtain the product 7 - carbonyl - 8, 15 - ISO pimaric acid methyl ester, by checking its GC purity of 98.5%. The preparation method is simple in operation, raw material sources are extensive, less environmental pollution, high purity of the product. (by machine translation)
Reaction with Paraform of Isomeric Olefins from Pimaric Series on Askanite-Bentonite Clay
Kuzakov,Shmidt,Korchagina,Bagryanskaya,Gatilov,Barkhash
, p. 1400 - 1408 (2007/10/03)
Under conditions of basic catalysis reaction of 3-methyl-3-cyanocyclopropene with S-methyl-isothiuronium salt yielded isomeric 1-methylthio-3-methyl-3-cyanocyclopropanes. The free S-methylthiourea is presumed to act as sulfiding reagent.
Condensation of Methyl Isopimarate with α,β-Unsaturated Aldehydes on Zeolites
Kuzakov, E. V.,Shmidt, E. N.,Bagryanskaya, I. Yu.,Rybalova, T. V.,Gatilov, Yu. V.,Barkhash, V. A.
, p. 171 - 178 (2007/10/02)
Reactions of methyl isopimarate with α-methylacrolein and acrolein over zeolites occur by two parallel pathways, Δ8(14)- and Δ8(9)-ene condensation, the former pathway being predominant.Under selected conditions, products of Δ8(14)-ene condensation undergo further conversions, namely intramolecular reaction of the aldehyde group with the double bond (similarly to cyclic Prins reaction) and cyclization of the resulting alcohol with perhydrobenzanthrene core to form an oxolane with a new type of skeleton.The direction of condensation of methylpimarate with unsaturated aldehydes is independent of the nature of enophiles and catalysts used.
Partial Synthesis of 9,10-Syn Diterpenes via Tosylhydrazone Reduction: (-)-(9β)-Pimara-7,15-diene and (-)-(9β)-Isopimaradiene
Chu, Min,Coates, Robert M.
, p. 4590 - 4597 (2007/10/02)
(9β)-Pimara-7,15-diene (3), a proposed intermediate in the biosynthesis of the momilactone phytoalexins (1 and 2) from rice, and its C-13 epimer, (9β)-isopimara-7,15-diene (4), were synthesized from methyl pimara- and isopimara-8,15-dien-18-oates (8b and 8a, respectively).Allylic oxidation of 8a and 8b as well as the derived diterpene hydrocarbons 15a and 15b with chromium trioxide-dipyridine complex afforded 8,15-dien-7-ones 9a, 9b, 16a, and 16b (35-54percent).Lithium-ammonia reduction of 9a, 16a, and 16b gave predominantly trans,anti,trans-isopimara- and -pimara-15-en-7-ones 10, 17a, and 17b.In contrast, catecholborane reduction of the tosylhydrazones of 9a and 9b provided methyl (9β)-isopimara- and (9β)-pimara-7,15-dien-20-oates (23a and 23b) having the 9,10-syn stereochemistry.The parent diterpenes, 3 and 4, were obtained by carboxyl-to-methyl conversions.In a collaborative investigation 3 was tentatively identified as one of five diterpene hydrocarbons produced upon incubation of (E,E,E)-geranylgeranyl pyrophosphate with a crude enzyme extract from UV-treated rice plants.
METABOLITES OF THE HONEY MUSHROOM, Armillaria mellea
Ayer, William A.,Macaulay, John B.
, p. 7 - 14 (2007/10/02)
The fungus Armillaria mellea (Vahl ex.Fr.) Kummer is responsible for severe losses in timber and fruit production.The metabolites isolated when certain strains of this fungus are grown in liquid culture have been identified as diterpenoid acids posessing the abietane (1) and pimarane (2) skeletons.These compounds, known collectively as resin acids, have not been reported previously from fungal source.In addition to the resin acids dehydroabietic acid (3), pimaric acid (4), isopimaric acid (5), and sandaracopimaric acid (6), three additional acids, levopimaric acid endo-peroxide (7), 7-oxodehydroabietic acid (9), and 7-oxo-15-hydroxydehydroabietic acid (10) were obtained.On one accasion three orange pigments, austocystin F (11), averufin (12), and averufanin (13), all previously known fungal metabolites, were isolated.
PART I. EPOXYDES DITERPENIQUES : SYNTHESE ET REACTIVITE D'EPOXYDES DERIVES D'ACIDES RESINIQUES
Papillaud, B.,Tiffon, F.,Taran, M.,Miguel, B. Arreguy-San,Delmond, B.
, p. 1845 - 1858 (2007/10/02)
Epoxidation of methyl esters of resin acids with the pimarane skeleton with p-nitroperbenzoic acid has permitted the isolation of epoxides of the intracyclic double bond.Allylic diterpenic alcohols were obtained by acid-catalysed isomerisation of diterpene epoxides, and the action of Collins reagent on these allylic alcohols has been studied.
