Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.
Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.
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DOI：
10.1021/jo1003136
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发表时间：
2010-05-07
影响因子：
3.6
通讯作者：
Pandey, Siyaram
中科院分区：
文献类型：
--
作者：
Collins, Jonathan;Rinner, Uwe;Moser, Michael;Hudlicky, Tomas;Ghiviriga, Ion;Romero, Anntherese E.;Kornienko, Alexander;Ma, Dennis;Griffin, Carly;Pandey, Siyaram
报道了7-脱氧潘生丁C-1衍生物的有效合成方法。关键步骤包括以下：在氮丙啶存在下用乙炔铝选择性地打开环氧化物;固态硅胶催化的氮丙啶打开;菲核的氧化裂解及其环化为菲酮以提供关键的C-1醛22。该醛转化为C-1乙酰氧基甲基和C-1羟甲基衍生物的描述沿着其对几种癌细胞系的生物活性的评价和细胞凋亡研究。C-1乙酰氧基甲基衍生物已显示出与天然产物相当的有前途的活性。此外，还报道了以醛22为起始原料的反式-二水解coricidine的全合成和7-脱氧pancratistatin的正式全合成。详细的实验和光谱数据提供了所有新的化合物。
An efficient synthesis of C-1 derivatives of 7-deoxypancratistatin is reported. The key steps include the following: selective opening of an epoxide with aluminum acetylide in the presence of an aziridine; solid-state silica-gel-catalyzed opening of an aziridine; oxidative cleavage of a phenanthrene core and its recyclization to phenanthridone to provide the key C-1 aldehyde 22. The conversion of this aldehyde to C-1 acetoxymethyl and C-1 hydroxymethyl derivatives is described along with the evaluation of their biological activity against several cancer cell lines and in an apoptosis study. The C-1 acetoxymethyl derivative has shown promising activity comparable to that of the natural product. In addition, a total synthesis of trans-dihydrolycoricidine and a formal total synthesis of 7-deoxypancratistatin are reported from aldehyde 22. Detailed experimental and spectral data are provided for all new compounds.
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影响因子：
2.1
作者：
Doyle, TJ;Hendrix, M;Haseltine, J
通讯作者：
Haseltine, J
影响因子：
5.1
作者：
GABRIELSEN, B;MONATH, TP;PHELAN, MJ
通讯作者：
PHELAN, MJ
影响因子：
3.6
作者：
CHIDA, N;OHTSUKA, M;OGAWA, S
通讯作者：
OGAWA, S
影响因子：
1.6
作者：
HAGIWARA, H;AKAMA, T;UDA, H
通讯作者：
UDA, H
影响因子：
5.2
作者：
Collins, Jonathan;Drouin, Melissa;Hudlicky, Tomas
通讯作者：
Hudlicky, Tomas