Stereoselective synthesis of fully substituted ethylenes via an Ag-catalyzed 1,6-nucleophilic addition/annulation cascade

2020 ◽  
Vol 56 (56) ◽  
pp. 7749-7752
Author(s):  
Bu-Zheng Tang ◽  
Wen-Juan Hao ◽  
Jia-Zhuo Li ◽  
Shan-Shan Zhu ◽  
Shu-Jiang Tu ◽  
...  

A catalytic 1,6-nucleophilic addition/annulation cascade was developed for the first time, and used to produce 27 hitherto unreported ethylene-linked 1-naphthol-imidazole pairs with generally good yields and complete stereoselectivity.

2022 ◽  
Author(s):  
Zhi-Gang Yin ◽  
Xiong-Wei Liu ◽  
Hui-Juan Wang ◽  
Min Zhang ◽  
Xiong-Li Liu ◽  
...  

A highly efficient synthesis of structurally diverse ortho-acylphenol–diindolylmethane hybrids 3 using carboxylic acid-activated chromones as versatile synthetic building blocks is reported here for the first time, through 1,4-nucleophilic addition and followed by a decarboxylation and pyrone ring opening reaction process.


2020 ◽  
Vol 18 (24) ◽  
pp. 4566-4568
Author(s):  
Gints Smits ◽  
Ronalds Zemribo

The core structure of eleganine A – a cytotoxic indole monoterpene alkaloid – was accessed for the first time.


Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 908-911 ◽  
Author(s):  
K. Babu ◽  
Arramshetti Venkanna ◽  
Borra Poornima ◽  
Bandi Siva ◽  
B. Babu

A stereoselective synthesis of the dibenzocyclooctadiene ­lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki–Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey–Bakshi–Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.


2012 ◽  
Vol 67 (4) ◽  
pp. 389-405 ◽  
Author(s):  
Ellen Klegraf ◽  
Horst Kunz

The stereoselective synthesis of 3-substituted and 3,4-disubstituted piperidine and piperidin-2-one derivatives was achieved starting from 2-pyridone. After N-galactosylation and subsequent O-silylation, nucleophilic addition of organometallic reagents proceeded with high regio- and stereoselectivity at 4-position. Substituents at position 3 were stereoselectively introduced by reaction of electrophiles with amide enolates of the N-galactosyl-2-piperidones.


2021 ◽  
Author(s):  
Bin Zheng ◽  
Chao Hang ◽  
Jason Zhu ◽  
Geoffrey Purdum ◽  
Melda Sezen-Edmonds ◽  
...  

A highly stereoselective synthesis of a cyclic dinucleotide (CDN) STING agonist containing two chiral thiophosphoramidate linkages is described. These rare, yet key functional groups were, for the first time, installed efficiently and with high diastereoselectivity using a specially designed P(V) reagent. By utilizing this strategy, the CDN was prepared in greater than sixteen-fold higher yield than the prior P(III) approach, with fewer hazardous reagents and chromatographic purifications.


Sign in / Sign up

Export Citation Format

Share Document