A practical synthesis of betulinic acid

被引:70
作者
Csuk, Rene [1 ]
Schmuck, Kianga [1 ]
Schaefer, Renate [1 ]
机构
[1] Univ Halle Wittenberg, Inst f Organ Chem, D-06120 Halle, Germany
关键词
LUPANE TRITERPENES; DERIVATIVES; OXIDATION; AGENTS;
D O I
10.1016/j.tetlet.2006.10.004
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学];
摘要
A new synthetic route for the synthesis of betulinic acid from betulin has been developed. The main step of this procedure is the selective oxidation of the primary alcohol function of betulin without affecting the secondary hydroxyl group. Applying shorter reaction times and lower temperatures results in the exclusive formation of the corresponding aldehyde, betulinal. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8769 / 8770
页数:2
相关论文
共 27 条
[1]
Betulinic acid derivatives as HIV-1 antivirals [J].
Aiken, C ;
Chen, CH .
TRENDS IN MOLECULAR MEDICINE, 2005, 11 (01) :31-36
[2]
Oxidation of betulin and its monoacetates by "activated" DMSO [J].
Ashavina, OY ;
Flekhter, OB ;
Galin, FZ ;
Kabal'nova, NN ;
Baltina, LA ;
Tolstikov, GA .
CHEMISTRY OF NATURAL COMPOUNDS, 2003, 39 (02) :207-211
[3]
Lupane triterpenes and derivatives with antiviral activity [J].
Baltina, LA ;
Flekhter, OB ;
Nigmatullina, LR ;
Boreko, EI ;
Pavlova, NI ;
Nikolaeva, SN ;
Savinova, OV ;
Tolstikova, GA .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (20) :3549-3552
[4]
Bender C., 2003, Ger. Patentschrift, Patent No. [DE 10204278 CI, 20030807, 10204278]
[5]
BHATTACHARYYA J, 1976, PHYTOCHEMISTRY, V15, P431
[6]
BI Y, 2005, ZHONGGUO XINYAO ZAZH, V14, P23
[7]
DRAGER B, 1998, Patent No. 19713768
[8]
Galgon T, 1999, PHYTOCHEM ANALYSIS, V10, P187, DOI 10.1002/(SICI)1099-1565(199907/08)10:4<187::AID-PCA443>3.0.CO
[9]
2-K
[10]
A concise semi-synthetic approach to betulinic acid from betulin [J].
Kim, DSHL ;
Chen, ZD ;
Nguyen, VT ;
Pezzuto, JM ;
Qiu, SX ;
Lu, ZZ .
SYNTHETIC COMMUNICATIONS, 1997, 27 (09) :1607-1612