Asymmetric Total Synthesis and Biological Evaluation of Proapoptotic Natural Myrcene-Derived Cyclohexenyl Chalcones

2018 ◽  
Vol 2018 (42) ◽  
pp. 5830-5835 ◽  
Author(s):  
Shelly Gapil Tiamas ◽  
Florian Audet ◽  
Alma Abou Samra ◽  
Jérome Bignon ◽  
Marc Litaudon ◽  
...  
2020 ◽  
Vol 22 (2) ◽  
pp. 584-588 ◽  
Author(s):  
Ke-Qiang Hou ◽  
Xue-Ping Chen ◽  
Yiyou Huang ◽  
Albert S. C. Chan ◽  
Hai-Bin Luo ◽  
...  

Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 213-224 ◽  
Author(s):  
Stephanie McCabe ◽  
Peter Wipf

The first total synthesis of natural (+)-cycloclavine uses a catalytic­ asymmetric cyclopropanation of allene, a regiospecific Pd-catalyzed­ enone formation, and two intramolecular Diels–Alder reactions for indole/indoline annulations. The binding properties of natural (+)- and unnatural (–)-cycloclavine on 16 CNS receptors revealed significant stereospecificity and unique binding profiles in comparison to LSD, psilocin, and DMT. Differential 5-HT affinities, as well as novel sigma­-1 receptor properties bode well for potential therapeutic developments of clavine alkaloid scaffolds.


Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3224
Author(s):  
Leander Geske ◽  
Ulrich Kauhl ◽  
Mohamed E. M. Saeed ◽  
Anja Schüffler ◽  
Eckhard Thines ◽  
...  

The biological activities of shancigusin C (1) and bletistrin G (2), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (1) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (2) was achieved by the Wittig olefination followed by several regioselective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (1) and bletistrin G (2) against tumor cells suggest suitability as a starting point for further structural variation.


2017 ◽  
Vol 33 (6) ◽  
pp. 890-894 ◽  
Author(s):  
Bohua Long ◽  
Jingzhao Zhang ◽  
Xueyan Wang ◽  
Xudong Tang ◽  
Zhengzhi Wu

2009 ◽  
Vol 131 (30) ◽  
pp. 10587-10597 ◽  
Author(s):  
K. C. Nicolaou ◽  
Xiao-Shui Peng ◽  
Ya-Ping Sun ◽  
Damien Polet ◽  
Bin Zou ◽  
...  

2018 ◽  
Vol 57 (34) ◽  
pp. 11020-11024 ◽  
Author(s):  
Hiromu Hattori ◽  
Joel Roesslein ◽  
Patrick Caspers ◽  
Katja Zerbe ◽  
Hideki Miyatake-Ondozabal ◽  
...  

2009 ◽  
Vol 15 (46) ◽  
pp. 12807-12818 ◽  
Author(s):  
Haruhiko Fuwa ◽  
Asami Saito ◽  
Shinya Naito ◽  
Keiichi Konoki ◽  
Mari Yotsu-Yamashita ◽  
...  

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