Procedure-Economical, Enantioselective Total Syntheses of Polycyclic Natural Products and Analogues Containing a 3a-Hydroxyhexahydropyrrolo[2,3-b]indole-2-carboxylic Acid Residue
Procedure-Economical, Enantioselective Total Syntheses of Polycyclic Natural Products and Analogues Containing a 3a-Hydroxyhexahydropyrrolo[2,3-b]indole-2-carboxylic Acid Residue
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含有 3a-羟基六氢吡咯并[2,3-b]吲哚-2-羧酸残基的多环天然产物和类似物的经济、对映选择性全合成
DOI：
10.1055/s-0040-1707164
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发表时间：
2020-06
期刊：
影响因子：
2
通讯作者：
Huang Pei-Qiang
中科院分区：
文献类型：
--
作者：
Huang Pei-Qiang
Abstract The 3a-hydroxyhexahydropyrrolo[2,3-b]indole-2-carboxylic acid (HPIC) residue and its aza-analogue are found in many bioactive natural products. In this account, short divergent total syntheses of several such natural products, diastereomers and analogues are described. It is demonstrated that by appropriate combination of different efficient tactics such as biomimetic/bio-inspired synthesis, chemo/regioselective reactions, umpolung of regioselectivity and/or reactivity, and tandem reactions, the enantioselective syntheses of polycyclic molecules such as (+)-asperlicin E and (–)-robustanoids A and B can be achieved in a protecting-group-free and redox-economical manner, in only three to four steps starting from l-tryptophan. 1 Introduction 2 Strategic Considerations 2.1 Occurrence of HO-HPIC and HO-aza-HPIC Residues in Natural Products 2.2 Biosyntheses of HO-HPIC and HO-aza-HPIC Residues 2.3 Chemical Syntheses of HO-HPIC and HO-aza-HPIC Residues 3 Procedure-Economical Syntheses of HO-HPIC-Containing Natural Products 3.1 Protecting-Group-Free Syntheses of Asperlicin E, Its Diastereomer, and an Analogue 3.2 Divergent Syntheses of (–)-Robustanoids A and B, a Diastereomer, and Analogues 4 Conclusion and Future Perspectives
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影响因子：
5.2
作者：
Kevin Greenman;Dana M. Hach;D. L. Van Vranken
通讯作者：
Kevin Greenman;Dana M. Hach;D. L. Van Vranken
影响因子：
1.8
作者：
D. Shi;Liangce Rong;Juxian Wang;Qiya Zhuang;Xiang-Shan Wang;Hongwen Hu
通讯作者：
D. Shi;Liangce Rong;Juxian Wang;Qiya Zhuang;Xiang-Shan Wang;Hongwen Hu
影响因子：
2.6
作者：
Sorra, Kumaraswamy;Mukkanti, K.;Pusuluri, Srinivas
通讯作者：
Pusuluri, Srinivas
影响因子：
2.1
作者：
Büchel, E;Martini, U;Sterner, O
通讯作者：
Sterner, O
DOI：
10.1002/9783527634606
发表时间：
2011-04
期刊：
--
影响因子：
--
作者：
E. Poupon;B. Nay
通讯作者：
E. Poupon;B. Nay