17751-36-9Relevant academic research and scientific papers
REACTIONS OF DITERPENOIDS ON SOLID SUPPORTS. I. OXIDATION OF METHYL ABIETATE ON THE SORBENTS Al2O3 AND SiO2 CONTAINING POTASSIUM PERMANGANATE
Kuzakov, E.V.,Shmidt, E.N.,Bagryanskaya, I.Yu.,Gatilov, Yu.V.
, p. 339 - 345 (1994)
The oxidation of methyl abietate on the sorbents Al2O3 and SiO2 containing potassium permanganate has benn studied.It has been shown that the following are formed under the conditions selected: compounds of the dehydroabietane series, stereoisomeric mono- and diepoxides of methyl abietate, and the products of their transformation on the sorbents.The structures and stereochemistries of the compounds isolated have been established with the aid of spectral methods and XSA.
Aerobic oxidation of 8,11,13-abietatrienes catalyzed by N-hydroxyphthalimide combined with 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) and its application to synthesis of naturally occurring diterpenes
Matsushita, Yoh-ichi,Sugamoto, Kazuhiro,Iwakiri, Yoshihisa,Yoshida, Satoru,Chaen, Takehito,Matsui, Takanao
experimental part, p. 3931 - 3934 (2010/08/07)
Methyl 8,11,13-abietatriene-18-oate (1b) and 7-oxo-8,11,13-abietatrienes 10 and 15 were converted into 15-hydroperoxy-7-oxo-8,11,13-abietatrienes 13 and 16 by aerobic oxidation catalyzed by N-hydroxyphthalimide (NHPI) combined with 2,2′-azobis(4-methoxy-2
Regioselective routes towards 14-hydroxyabietane diterpenes. A formal synthesis of immunosuppressant (-)-triptolide from (+)-abietic acid
Alvarez-Manzaneda, Enrique,Chahboun, Rachid,Bentaleb, Faouzia,Alvarez, Esteban,Escobar, M. Angeles,Sad-Diki, Said,Cano, Maria José,Messouri, Ibtissam
, p. 11204 - 11212 (2008/02/13)
Two procedures to introduce an oxygenated function into the C-14 of abietane diterpenes with complete regioselectivity have been developed. Utilizing these, the synthesis of the antileishmanial quinone (-)-12-deoxyroyleanone (1) and a formal synthesis of antitumour and immunosuppressant (-)-triptonide (7) and (-)-triptolide (8) from (+)-abietic acid (13) have been carried out.
Preparation of potential anti-inflammatory agents from dehydroabietic acid
Li,McChesney
, p. 646 - 651 (2007/10/02)
Methyl 16-nor-16-carboxydehydroabietate (22), 16-nor-16- carboxydehydroabietinol acetate (23), methyl 7-keto-16-nor-16- carboxydehydroabietate (29), 16-nor-16-carboxydehydroabietic acid (30), 16- nor-16-carboxydehydroabietinol (31), 7-keto-16-nor-16-carboxydehydroabietic acid (32), methyl 7-hydroxy-16-nor-16-carboxydehydroabietate (33), and 7- hydroxy-16-nor-16-carboxydehydroabietic acid (34) were prepared from dehydroabietic acid. Only 22 and 32 had weak anti-inflammatory activity.
Investigation of the Allergenic Principles from Colophony: Autoxidation, Synthesis, and Sensitization
Krohn, Karsten,Budianto, Emil,Floerke, Ulrich,Hausen, Bjoern M.
, p. 911 - 920 (2007/10/02)
The autoxidation of abietic acid (1a), levopimaric acid (2a), and dehydroabietic acid (3a) was studied and the compounds 3a as well as (after esterification) 8b, 9b, 10b, 11b (from 1a); 6b (from 2a); and 4b, 5b (from 3a) were isolated for the first time.Some derivatives (6a, 6b, 13b/14b, and 7b) were semi-synthezised.The isolated autoxidation products, the synthetic compounds and some polar fractions of natural colophony were tested for their sensitizing capacity.Compounds 4a, 10b, 16, and 18 as well as the combined polar fraction A-D of colophony show enhanced sensitizing capacity.Methylation of the acids to the ester significantly reduces their activity.Key Words: Resin acids, autoxidation of / Colophony, allergy of / Sensitizing potency
Electrooxidative Functionalizations of Dehydroabietic Acid
Uneyama, Kenji,Katayama, Tatsuo,Torii, Sigeru
, p. 3043 - 3044 (2007/10/02)
Dehydroabietic acid methyl ester (1) was converted into 7-acetoxydehydroabietic acid methyl ester by direct electrooxidation in acetic acid and 7-oxodehydroabietic acid methyl ester by ruthenium dioxide-mediated oxidation.Non-Kolbe type electrodecarboxylation of 1 resulted in the introduction of a double bond into the ring A of 1.
REGIOSELECTIVE REACTIONS OF ABIETIC ACID METHYL ESTER
Escudero, Javier,Marquez, Cecilio,Rabanal, Rosa Ma,Valverde, S.
, p. 3167 - 3170 (2007/10/02)
Ozonolysis of abietic acid methyl ester 1 in the presence of mercuric acetate afforded the 13,14-seco-derivative in fair yield (50percent).Selenium dioxide oxidation of 1 in t-butanol gave 9-α-hydroxy-abietic acid methyl ester 6, dehydroabietic acid methyl ester 4 and its 7α-hydroxy-derivative 4b.
Collins Oxidation of Methyl (+)-13β-Abiet-8-en-18-oate and Absolute Configuration of Suaveolic Acid
Matsumoto, Takashi,Imai, Sachihiko,Yuki, Shuhei,Katayama, Arata,Furutani, Manabu
, p. 527 - 533 (2007/10/02)
The oxidation of methyl (+)-13β-abiet-8-en-18-oate with Collins reagent yielded nine oxidation products.Their structures were elucidated on the basis of spectroscopic and chemical data to be methyl (-)-14-hydroxy-7-oxoabieta-8,11,13-trien-18-oate (1percent yield), methyl (-)-11,14-dioxoabieta-8,12-dien-18-oate (1percent), methyl (+)-11-oxo-13β-abiet-8-en-18-oate (18percent), methyl (-)-8α,9α-epoxy-7-oxo-13β-abietan-18-oate (2percent), methyl(+)-7-oxoabieta-8,11,13-trien-18-oate (2percent), methyl (+)-11,14-dihydroxy-7-oxoabieta-8,11,13-trien-18-oate (2percent), methyl (+)-7,11-dioxo-13β-abiet-8-en-18-oate (17percent), methyl(+)-14-oxo-13β-abiet-8-en-18-oate (15) (4percent), and methyl (+)-7-oxo-13β-abiet-8-en-18-oate (23percent) respectively.It is noteworthy that oxygenation occurs not only at the C-7 and C-11 positions but also at the C-14 position.The oxygenated products obtained in this studies could be useful intermediates for the synthesis of the oxidized diterpenoids of abietane skeleton.To exemplify this, 15 was converted to methyl suaveolate and suaveolol.Hydrolysis of the former yielded suaveolic acid, thus confirming its absolute configuration to be 4R, 5R, 10S, 13S, and 14S.
