67119-95-3Relevant academic research and scientific papers
First enantiospecific synthesis of antileishmanial 12-deoxyroyleanone from abietic acid
Alvarez-Manzaneda Roldán,Chahboun,Bentaleb,Cabrera Torres,Alvarez,Haidour,Ramos López,Alvarez-Manzaneda Roldán,El Houssame
, p. 2701 - 2704 (2004)
12-Deoxyroyleanone (1), an abietane diterpenoid with appreciable antileishmanial activity, has been efficiently synthesized from abietic acid (10; 11 steps for a 25% overall yield).
Synthesis of 12-deoxyroyleanone, cryptoquinone, 11,14-dihydroxy-8,11,13- abietatrien-7-one, and related derivatives from dehydroabietic acid
Matsushita, Yoh-Ichi,Iwakiri, Yoshihisa,Yoshida, Satoru,Sugamoto, Kazuhiro,Matsui, Takanao
, p. 3629 - 3632 (2005)
Naturally occurring abietane quinones and hydroquinone, namely, 12-deoxyroyleanone (1a), cryptoquinone (4a), and 11,14-dihydroxyabieta-8,11,13- trien-7-one (5a), together with the epimers of tryptoquinones D (2) and F (3), were first synthesized from dehydroabietic acid (6).
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.
Asymmetric synthesis of abietane diterpenoids via B-alkyl Suzuki-Miyaura coupling. Formal total asymmetric synthesis of 12-deoxyroyleanone and cryptoquinone
Yajima, Arata,Yamaguchi, Ayumi,Saitou, Fumihiro,Nukada, Tomoo,Yabuta, Goro
, p. 1080 - 1084 (2007/10/03)
A convergent synthetic strategy for abietane diterpenoids via B-alkyl Suzuki-Miyaura coupling and Lewis acid-mediated cyclization reactions is established. Asymmetric total synthesis of 12-deoxyroyleanone, an antileishmanial diterpene, is described.
Studies with plant-cell cultures of the Chinese herbal plant, Tripterygium wilfordii. Isolation and characterization of diterpenes
Kutney, James P.,Han, Kang
, p. 77 - 93 (2007/10/03)
A detailed analysis of the established cell-culture line (coded as TRP4a) of the important Chinese herbal plant, Tripterygium wilfordii, in terms of diterpene production, is presented. In this study, 28 diterpenes have been isolated and characterized. Of these, 26 were isolated for the first time from the TRP4a cell line, 8 were novel compounds. From an analysis of the diterpenes obtained, a biosynthetic pathway of the pharmacologically interesting triepoxide, tripdiolide 29, is proposed.
SYNTHESES OF OPTICALLY ACTIVE (+)-FRAGROLIDE AND (+)-BEMADIENOLIDE FROM DEHYDROABIETIC ACID
Akita, Hiroyuki,Anazawa, Akira,Oishi, Takeshi
, p. 1588 - 1593 (2007/10/02)
14-Hydroxydehydroabietane derivatives (8 and 9), having an oxygen functional group at the 6-position, were obtained from 14-hydroxy-7-oxodehydroabietane (10) by transformation of the 7-oxo group into a 6-acetoxyl (or hydroxyl) group.Ozonolysis of the above phenols (8 and 9) and subsequent reduction gave the 6-oxygenated confertifolin derivatives 17 and 19, respectively.Oxidation of 6-hydroxyconfertifolin (19) afforded the optically active (+)-fragrolide (4).On the other hand, 19 was also converted into (+)-bemadienolide (5) by oxidation of the important intermediate, 6β-phenylselenoconfertifolin (25).Keywords: - aromatic ring cleavage; drimanic sesquiterpenes; phenolic diterpenes; ozonolysis; transfer of ketone
