Regioselective routes towards 14-hydroxyabietane diterpenes. A formal synthesis of immunosuppressant (-)-triptolide from (+)-abietic acid

被引:45
作者
Alvarez-Manzaneda, Enrique [1 ]
Chahboun, Rachid [1 ]
Bentaleb, Faouzia [1 ]
Alvarez, Esteban [1 ]
Escobar, M. Angeles [1 ]
Sad-Diki, Said [1 ]
Cano, Maria Jose [1 ]
Messouri, Ibtissam [1 ]
机构
[1] Univ Granada, Fac Ciencias, Inst Biotechnol, Dept Quim Organ, E-18071 Granada, Spain
关键词
D O I
10.1016/j.tet.2007.07.088
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
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. (c) 2007 Published by Elsevier Ltd.
引用
收藏
页码:11204 / 11212
页数:9
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