An Efficient Synthesis of Cyclic IDP- and Cyclic 8-Bromo-IDP-Carbocyclic-Riboses Using a Modified Hata Condensation Method To Form an Intramolecular Pyrophosphate Linkage as a Key Step. An Entry to a General Method for the Chemical Synthesis of Cyclic ADP-Ribose Analogues1

2000 ◽  
Vol 65 (17) ◽  
pp. 5238-5248 ◽  
Author(s):  
Masayoshi Fukuoka ◽  
Satoshi Shuto ◽  
Noriaki Minakawa ◽  
Yoshihito Ueno ◽  
Akira Matsuda
2016 ◽  
Vol 138 (10) ◽  
pp. 3553-3561 ◽  
Author(s):  
Ji-Shen Zheng ◽  
Yao He ◽  
Chao Zuo ◽  
Xiao-Ying Cai ◽  
Shan Tang ◽  
...  

2014 ◽  
Vol 908 ◽  
pp. 211-214
Author(s):  
Zhen Biao Xie ◽  
Shan Shan Gong ◽  
Qi Sun

The diphosphate and triphosphate of an antiviral 2’,3’-dideoxynucleoside, d4T, were synthesized via a P(V)–N activation method. The key d4T phosphoropiperidate intermediate was obtained by a redox condensation method based on 2,2’-dithiodipyridine/triphenylphosphine system. The reaction of the phosphoropiperidate with phosphate and pyrophosphate in the presence of acidic 4,5-dicyanoimidazole activator afforded the desired d4T diphosphate and triphosphate in high isolated yields.


2021 ◽  
Author(s):  
Robert F. Lusi ◽  
Goh Sennari ◽  
Richmond Sarpong

<p>Natural product total synthesis inspires strategy development in chemical synthesis. In the 1960s, Corey and coworkers demonstrated a visionary preparation of the terpenoid longifolene, using “strategic bond analysis” to craft a synthesis route. This approach proposes that efficient synthesis routes to bridged, polycyclic, structures should be formulated to introduce the bulk of the target’s topological complexity at a late stage. In subsequent decades, similar strategies have proved general for the syntheses of a wide variety of bridged, polycyclic molecules. Here, we demonstrate that an orthogonal strategy, which utilizes a topologically complex bicyclo[2.2.1] starting material accessed through a scaffold rearrangement of (<i>S</i>)-carvone, leads to a remarkably short synthesis of the longifolene-related terpenoid longiborneol. We also employ a variety of late-stage C–H functionalization tactics in divergent syntheses of many longiborneol congeners. Our strategy should prove effective for the preparation of other topologically complex natural products that contain the bicyclo[2.2.1] framework.</p>


2020 ◽  
Vol 56 (91) ◽  
pp. 14239-14242
Author(s):  
Toshiki Takei ◽  
Tomoshige Ando ◽  
Toshifumi Takao ◽  
Yusuke Ohnishi ◽  
Genji Kurisu ◽  
...  

Selenoferredoxin, in which four selenocysteine residues are coordinated to the 2Fe2S cluster, was successfully synthesized using the segment condensation method.


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