Regioselective routes towards 14-hydroxyabietane diterpenes. A formal synthesis of immunosuppressant (−)-triptolide from (+)-abietic acid |
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Authors: | Enrique Alvarez-Manzaneda,Rachid Chahboun,Faouzia Bentaleb,Esteban Alvarez,M. Angeles Escobar,Said Sad-Diki,Maria José Cano,Ibtissam Messouri |
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Affiliation: | Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain |
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Abstract: | 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. |
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