Catalytic enantioselective synthesis of indolizino[8,7-b]indole alkaloid derivatives based on the tandem reaction of tertiary enamides

2021 ◽  
Author(s):  
Xin-Ming Xu ◽  
Ming Xie ◽  
Jiazhu Li ◽  
Mei-Xiang Wang
Keyword(s):  
Indole Alkaloid ◽  
Enantioselective Synthesis ◽  
High Yield ◽  
Tandem Reaction ◽  
Indole Derivatives

An exquisite Pybox/Cu(OTf)2-catalyzed asymmetric tandem reaction of tertiary enamides was developed, which enabled the expeditious synthesis of indolizino[8,7-b]indole derivatives in high yield, excellent enantioselectivity and diastereoselectivity.

Synthesis of 1,2,3-Triazole-Fused Indole Derivatives via Copper-Catalyzed Cascade Reaction

Synthesis ◽  
2021 ◽  
Author(s):  
Fengtao Zhou ◽  
Qiuyu Zhang ◽  
Kashif Majeed ◽  
Bangjie Liu
Keyword(s):  
Quantum Efficiency ◽  
Photophysical Properties ◽  
Cascade Reaction ◽  
Tandem Reaction ◽  
Indole Derivatives ◽  
Wide Range

AbstractA copper-catalyzed tandem reaction has been developed for the synthesis of 1,2,3-triazole-fused indole derivatives. This protocol allowed us to access a wide range of 1,2,3-triazole-fused indole derivatives in moderate to excellent yields. The 1,2,3-triazole-fused indole derivatives emit blue and greenish light when excited at 365 nm. The products were further explored for their quantum efficiency and photophysical properties.

Assembly of Fluorinated Chromanones via Enantioselective Tandem Reaction

2021 ◽  
Author(s):  
Mengxue Lu ◽  
Zongli Xiong ◽  
Yuqiao Zhou ◽  
Xin Wang ◽  
Xiaoyi Li ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Tandem Reaction ◽  
Unsaturated Aldehydes ◽  
Stereogenic Centers ◽  
First Time

The enantioselective synthesis of fluorinated tricyclic chromanones with multiple vicinal stereogenic centers has been realized for the first time, through the tandem reaction between 2-fluorinated 1-(2-hydroxyaryl)-1,3-diketones and α,β-unsaturated aldehydes. In...

Enantioselective synthesis of (R)-tolterodine using lithiation/borylation–protodeboronation methodology

2012 ◽  
Vol 90 (11) ◽  
pp. 965-974 ◽  
Author(s):  
Stefan Roesner ◽  
Varinder K. Aggarwal
Keyword(s):  
Enantioselective Synthesis ◽  
High Yield ◽  
Magnesium Bromide ◽  
Efficient Synthesis ◽  
Boronic Ester ◽  
Better Than

The synthesis of the pharmaceutical (R)-tolterodine is reported using lithiation/borylation–protodeboronation of a homoallyl carbamate as the key step. This step was tested with two permutations: an electron-neutral aryl Li-carbamate reacting with an electron-rich boronic ester and an electron-rich aryl Li-carbamate reacting with an electron-neutral boronic ester. It was found that the latter arrangement was considerably better than the former. Further improvements were achieved using magnesium bromide in methanol leading to a process that gave high yield and high enantioselectivity in the lithiation/borylation reaction. The key step was used in an efficient synthesis of (R)-tolterodine in a total of eight steps in a 30% overall yield and 90% ee.

scholarly journals Efficient production of vindoline from tabersonine by metabolically engineered Saccharomyces cerevisiae

2021 ◽  
Vol 4 (1) ◽  
Author(s):  
Tengfei Liu ◽  
Ying Huang ◽  
Lihong Jiang ◽  
Chang Dong ◽  
Yuanwei Gou ◽  
...  
Keyword(s):  
Cytochrome P450 ◽  
De Novo ◽  
Indole Alkaloid ◽  
Functional Expression ◽  
High Yield ◽  
Efficient Production ◽  
Cytochrome P450 Enzymes ◽  
Copy Numbers ◽  
Yield Production ◽  
Engineered Saccharomyces Cerevisiae

AbstractVindoline is a plant derived monoterpene indole alkaloid (MIA) with potential therapeutic applications and more importantly serves as the precursor to vinblastine and vincristine. To obtain a yeast strain for high yield production of vindoline from tabersonine, multiple metabolic engineering strategies were employed via the CRISPR/Cas9 mediated multiplex genome integration technology in the present study. Through increasing and tuning the copy numbers of the pathway genes, pairing cytochrome P450 enzymes (CYPs) with appropriate cytochrome P450 reductases (CPRs), engineering the microenvironment for functional expression of CYPs, enhancing cofactor supply, and optimizing fermentation conditions, the production of vindoline was increased to a final titer as high as ∼16.5 mg/L, which is more than 3,800,000-fold higher than the parent strain and the highest tabersonine to vindoline conversion yield ever reported. This work represents a key step of the engineering efforts to establish de novo biosynthetic pathways for vindoline, vinblastine, and vincristine.

Pictet–Spengler reaction based on in situ generated α-amino iminium ions through the Heyns rearrangement

2020 ◽  
Vol 7 (20) ◽  
pp. 3242-3246
Author(s):  
Jun-xiu Liang ◽  
Guo-bin Yang ◽  
Yong-po Zhang ◽  
Dong-dong Guo ◽  
Jin-zhong Zhao ◽  
...  
Keyword(s):  
High Yield ◽  
Tandem Reaction ◽  
Iminium Ions

A useful tandem reaction via the Heyns rearrangement and Pictet–Spengler reaction was developed which ensured the synthesis of complex N-heteropolycycles containing tetrahydro-β-carboline with high yield (up to 96%) and dr (99 : 1).

Organocatalytic enantioselective synthesis of C3 functionalized indole derivatives

Tetrahedron ◽  
2016 ◽  
Vol 72 (49) ◽  
pp. 8042-8049 ◽  
Author(s):  
Jasneet Kaur ◽  
Nasarul Islam ◽  
Akshay Kumar ◽  
Vimal K. Bhardwaj ◽  
Swapandeep Singh Chimni
Keyword(s):  
Enantioselective Synthesis ◽  
Indole Derivatives
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