Robustanoids A and B, two novel pyrrolo[2,3-b]indole alkaloids from Coffea canephora: isolation and total synthesis,Organic Chemistry Frontiers

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Robustanoids A and B, two novel pyrrolo[2,3-b]indole alkaloids from Coffea canephora: isolation and total synthesis
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-11-01 00:00:00 , DOI: 10.1039/c7qo00931c
Jianxin Han _{1,

2,

3,

4,

5} , Sheng-Tong Niu _{1,

2,

3,

4,

5} , Yushuang Liu _{1,

2,

3,

4,

5} , Lishe Gan _{6,

7,

8,

9} , Tianfu Wang _{1,

2,

3,

4,

5} , Chong-Dao Lu _{1,

2,

3,

4,

5} , Tao Yuan _{1,

2,

3,

4,

5}

Affiliation

Two novel pyrrolo[2,3-b]indole alkaloids, named robustanoids A (1) and B (2), featuring an unprecedented 1,2,3,4,8b,8c-hexahydro-2a,4a-diazapentaleno[1,6-ab]indene moiety, were isolated from Coffea canephora beans. Their structures were determined by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculation. The total synthesis of compounds 1 and 2 was successfully conducted to give a decent total yield (∼29%) in 8 steps, which also confirmed the structures determined by spectroscopic data. Compound 2 showed α-glucosidase inhibitory activity comparable to that of the positive control, acarbose.

中文翻译：

Robustanoids A和B，两种新的来自咖啡粉的吡咯并[2,3- b ]吲哚生物碱：分离和全合成

两种新颖的吡咯并[2,3- b ]吲哚生物碱，分别称为健壮类动物A（1）和B（2），具有前所未有的1,2,3,4,8b，8c-hexahydro-2a，4a-diazapentaleno [1，从咖啡小豆中分离了6- ab ]茚基部分。通过广泛的光谱分析和电子圆二色性（ECD）计算确定了它们的结构。成功地进行了化合物1和2的全合成，分8步获得了可观的总收率（约29％），这也证实了由光谱数据确定的结构。化合物2显示出与阳性对照阿卡波糖相当的α-葡萄糖苷酶抑制活性。

更新日期：2017-11-08

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