22552-62-1Relevant academic research and scientific papers
Stereoselective transformations of (+)-abietic acid into (+)-vitedoin B and (+)-negundoin A
Tapia, Rubén,Bouanou, Hanane,Alvarez, Esteban,Alvarez-Manzaneda, Ramón,Chahboun, Rachid,Alvarez-Manzaneda, Enrique
, p. 4405 - 4413 (2014)
The first synthesis of spirolactone (+)-vitedoin B (14 steps, 8.0% global yield) and spiro enol ether (+)-negundoin A (19 steps, 3.7% global yield), via a nor-labdane acetoxy ester, has been achieved starting from commercial (+)-abietic acid.
First synthesis of antitumoral dasyscyphin B
Akhaouzan, Ali,Fernández, Antonio,Mansour, Ahmed I.,Alvarez, Esteban,Haid?ur, Ali,Alvarez-Manzaneda, Ramón,Chahboun, Rachid,Alvarez-Manzaneda, Enrique
, p. 6176 - 6185 (2013)
The first synthesis of dasyscyphin B, an antitumoral metabolite obtained from the ascomycete Dasyscyphus niveus, has been achieved starting from commercial abietic acid. The key steps of the synthetic sequence are the diastereoselective α-methylation of a ketoaldehyde, followed by an intramolecular aldol condensation and the further Diels-Alder cycloaddition of a dienol ester. The procedure reported will allow the synthesis of related metabolites functionalized in the A ring. The Royal Society of Chemistry.
Synthesis of complex and diverse compounds through ring distortion of abietic acid
Rafferty, Ryan J.,Hicklin, Robert W.,Maloof, Katherine A.,Hergenrother, Paul J.
supporting information, p. 220 - 224 (2014/01/17)
Many compound screening collections are populated by members that possess a low degree of structural complexity. In an effort to generate compounds that are both complex and diverse, we have developed a strategy that uses natural products as a starting point for complex molecule synthesis. Herein we apply this complexity-to-diversity approach to abietic acid, an abundant natural product used commercially in paints, varnishes, and lacquers. From abietic acid we synthesize a collection of complex (as assessed by fraction of sp 3-hybridized carbons and number of stereogenic centers) and diverse (as assessed by Tanimoto analysis) small molecules. The 84 compounds constructed herein, and those created through similar efforts, should find utility in a variety of biological screens. Abietic acid was used as the starting point for the synthesis of 84 complex and diverse small molecules. Their complexity was assessed by the fraction of sp3-hybridized carbon atoms and the number of stereogenic centers, and their diversity was evaluated by Tanimoto analysis. The 84 compounds constructed herein, and those created through similar efforts, should find utility in a variety of biological screens. Copyright
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.
SYNTHESIS OF (-)-AMBROX FROM l-ABIETIC ACID
Koyama, Hiroo,Kaku, Yumiko,Ohno, Masaji
, p. 2863 - 2866 (2007/10/02)
Synthesis of (-)-ambrox 1 has been completed stereoselectively starting from l-abietic acid 2 .
A New Synthesis of Desmethylambraoxide
Buchbauer, Gerhard,Heneis, Vera M.,Krejci, Viktoria,Talsky, Claudia,Wunderer, Hanneliese
, p. 1345 - 1358 (2007/10/02)
A new synthesis of the title compound starting from abietic acid is described.Regioselective osmylation of the Δ13,14-double bond of abietic acid methyl ester (6) and subsequent hydrogenation furnishes dihydrodihydroxyabietic acid methyl ester (12) with an all-trans-connection of the three rings.Periodate cleavage of 12 leads to 13 which can be transformed into the triester 14 by Baeyer-Villiger oxidation.The configuration of the aldehyde group in 13 as well of the formyloxy group in 14 has been ensured to be equatorial.LAH-reduction of 14 leads to the triol 16 which after cyclisation and reductive dehydroxylation furnishes the fragrance compound 4. - Keywords: Abietic acid; Ambergris fragrance compound; Baeyer-Villiger oxidation; Decahydro-1-naphthalene-carboxylic acid derivatives; Dodecahydro-1H-naphthopyrane derivatives; Periodate cleavage; Reductive dehydroxylation; Regioselective osmylation
