Regioselective Biomimetic Synthesis of Dimeric Oxyresveratrol Derivatives

Synlett ◽  
2020 ◽  
Vol 31 (18) ◽  
pp. 1809-1812
Author(s):  
Wenling Li ◽  
Lu Ran ◽  
Hongpeng Li ◽  
Ge Chao ◽  
Xiaodong Kang ◽  
...  
Keyword(s):  
Horseradish Peroxidase ◽  
Biomimetic Synthesis ◽  
Coupling Reactions ◽  
Wittig Reactions ◽  
Key Steps ◽  
Acetone System

AbstractOxyresveratrol and its methylated derivative as coupling precursors were efficiently prepared in four steps, with Wittig reactions and subsequent isomerization reactions as the key steps. The coupling reactions of oxyresveratrol under various oxidative conditions gave a complex and inseparable mixture of coupling products. The oxidative dimerizations of methylated oxyresveratrols catalyzed by horseradish peroxidase–H2O2 or FeCl3·6H2O in an acetone system predominantly produced the 8–5-coupled and 8–10-coupled dihydrobenzofuran-type dimers, respectively. This regioselective biomimetic strategy might be useful in synthesizing other dimeric oxyresveratrol derivatives.

scholarly journals Total syntheses of all tri-oxygenated 16-phytoprostane classes via a common precursor constructed by oxidative cyclization and alkyl–alkyl coupling reactions as the key steps

2017 ◽  
Vol 15 (44) ◽  
pp. 9408-9414 ◽  
Author(s):  
Jakub Smrček ◽  
Radek Pohl ◽  
Ullrich Jahn
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Common Precursor ◽  
Key Steps

A parallel total synthesis of 16-F1t-, 16-E1-phytoprostanes and a first synthesis of 16-D1t-phytoprostanes based on a common precursor are described.

scholarly journals First Stereoselective Total Synthesis of Ciryneol C

SynOpen ◽  
2019 ◽  
Vol 03 (02) ◽  
pp. 59-66
Author(s):  
Ambati Sharada ◽  
Lakshmi Srinivasa Rao Kundeti ◽  
Kallaganti V. S. Ramakrishna ◽  
Kommu Nagaiah
Keyword(s):  
Total Synthesis ◽  
Coupling Reactions ◽  
Asymmetric Total Synthesis ◽  
Acetylene Derivative ◽  
Wittig Olefination ◽  
Epoxide Opening ◽  
Key Steps

The acetylene derivative Ciryneol C was isolated from the roots of C. japonicum. The asymmetric total synthesis of Ciryneol C was achieved in seven steps, with Horner–Wittig olefination, regioselective epoxide opening, and Cadiot–Chodkiewicz coupling reactions being the key steps.

Design, chemical synthesis, and in vitro biological evaluation of simplified estradiol–adenosine hybrids as inhibitors of 17β-hydroxysteroid dehydrogenase type 1

2009 ◽  
Vol 87 (8) ◽  
pp. 1180-1199 ◽  
Author(s):  
Marie Bérubé ◽  
Donald Poirier
Keyword(s):  
Hydroxysteroid Dehydrogenase ◽  
Acid Group ◽  
Biological Evaluation ◽  
Benzene Derivative ◽  
Coupling Reactions ◽  
Cofactor Binding ◽  
Cross Metathesis ◽  
Key Steps

A series of estradiol (E2) derivatives were designed to interact with both the substrate- and the cofactor-binding sites of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1). These analogues of potent E2–adenosine hybrid inhibitor EM-1745, where the adenosine moiety was replaced by a more stable benzene derivative, were synthesized from estrone using alkene cross-metathesis and Sonogashira coupling reactions as key steps. In vitro biological evaluation of these steroid derivatives revealed that a spacer of 13 methylenes, between the 16β-position of E2 and the adenosine mimic bearing a carboxylic acid group, gave the best inhibition of 17β-HSD1.

scholarly journals Synthetic Studies of Enacyloxins: A Series of Antibiotics Isolated from Frateuria sp. W-315: C1′-C8′ and C9′-C15′ Fragments

2015 ◽  
Vol 10 (4) ◽  
pp. 1934578X1501000
Author(s):  
Aki Saito ◽  
Wataru Igarashi ◽  
Hiroyuki Furukawa ◽  
Hiroki Hoshikawa ◽  
Teiko Yamada ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Nucleophilic Substitution Reaction ◽  
Synthetic Studies ◽  
Wittig Reactions ◽  
Key Steps

Synthetic studies of enacyloxins (ENXs), a series of yellow-colored, polyene-polyol antibiotics produced by Frateuria sp. W-315, are described. The C1′-C8′ polyene fragments were prepared using successive Wittig reactions. The C9′-C15′ and C10′-C15′ fragments were constructed from ( S)-isopropylideneglyceraldehyde using Yamaguchi's nucleophilic substitution reaction of acetylide to epoxide, and/or Marshall's allenylindium mediated reaction as the key steps.

Second-generation total synthesis of aplyronine A featuring Ni/Cr-mediated coupling reactions

2017 ◽  
Vol 15 (1) ◽  
pp. 124-131 ◽  
Author(s):  
Ichiro Hayakawa ◽  
Keita Saito ◽  
Sachiko Matsumoto ◽  
Shinichi Kobayashi ◽  
Ayaka Taniguchi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Second Generation ◽  
Coupling Reactions ◽  
Key Steps ◽  
Aplyronine A

Second-generation total synthesis of aplyronine A, a potent antitumor marine macrolide, was achieved using Ni/Cr-mediated coupling reactions as key steps.

Enantioselective construction of substituted pyridine and seven-membered carbocyclic skeleton: Biomimetic synthesis of (-)-rupestine D, (-)-guaipyridine, (-)-epiguaipyridine, (-)-cananodine and their stereoisomers

2021 ◽  
Author(s):  
Cun Zhang ◽  
Bianlin Wang ◽  
Paruke Aibibula ◽  
Jiangyu Zhao ◽  
Haji Akber Aisa
Keyword(s):  
Biomimetic Synthesis ◽  
Key Steps ◽  
Carbocyclic Skeleton

The guaipyridine alkaloids (-)-rupestine D, (-)-guaipyridine, (-)-epiguaipyridine, (-)-cananodine together with two stereoisomers 8-epi-rupestine D, and 5-epi-cananodine were synthesized enantioselectively from readily available citronellol. The key steps in this synthesis are...

scholarly journals Biomimetic Synthesis of Resveratrol Trimers Catalyzed by Horseradish Peroxidase

Molecules ◽  
2017 ◽  
Vol 22 (5) ◽  
pp. 819 ◽  
Author(s):  
Jian-Qiao Zhang ◽  
Gan-Peng Li ◽  
Yu-Long Kang ◽  
Bin-Hao Teng ◽  
Chun-Suo Yao
Keyword(s):  
Horseradish Peroxidase ◽  
Biomimetic Synthesis
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