Stereochemically controlled synthesis of steroid side chains: synthesis of desmosterol

1980 ◽  
Vol 45 (6) ◽  
pp. 1172-1174 ◽  
Author(s):  
Masato Koreeda ◽  
Yoshio Tanaka ◽  
Anchel Schwartz
Keyword(s):  
Controlled Synthesis ◽  
Side Chains

scholarly journals Lactones in the Synthesis of Prostaglandins and Prostaglandin Analogs

2021 ◽  
Vol 22 (4) ◽  
pp. 1572
Author(s):  
Constantin Tănase ◽  
Lucia Pintilie ◽  
Raluca Elena Tănase
Keyword(s):  
Biological Role ◽  
Controlled Synthesis ◽  
Side Chains ◽  
Enzymatic Resolution ◽  
Marine Mollusc ◽  
Enantioselective Reactions ◽  
The Many ◽  
Key Steps

In the total stereo-controlled synthesis of natural prostaglandins (PGs) and their structural analogs, a vast class of compounds and drugs, known as the lactones, are encountered in a few key steps to build the final molecule, as: δ-lactones, γ-lactones, and 1,9-, 1,11-, and 1,15-macrolactones. After the synthesis of 1,9-PGF2α and 1,15-PGF2α lactones, many 1,15-lactones of E2, E3, F2, F3, A2, and A3 were found in the marine mollusc Tethys fimbria and the quest for understanding their biological role stimulated the research on their synthesis. Then 1,9-, 1,11-, and 1,15-PG lactones of the drugs were synthesized as an alternative to the corresponding esters, and the first part of the paper describes the methods used for their synthesis. The efficient Corey procedure for the synthesis of prostaglandins uses the key δ-lactone and γ-lactone intermediates with three or four stereocenters on the cyclopentane fragment to link the PG side chains. The paper describes the most used procedures for the synthesis of the milestone δ-Corey-lactones and γ-Corey-lactones, their improvements, and some new promising methods, such as interesting, new stereo-controlled and catalyzed enantioselective reactions, and methods based on the chemical/enzymatic resolution of the compounds in different steps of the sequences. The many uses of δ-lactones not only for the synthesis of γ-lactones, but also for obtaining 9β-halogen-PGs and halogen-substituted cyclopentane intermediates, as synthons for new 9β-PG analogs and future applications, are also discussed.

Copolymerization of l-lactide/trimethylene carbonate by organocatalysis: controlled synthesis of comb-like graft copolymers with side chains with different topologies

RSC Advances ◽  
2016 ◽  
Vol 6 (46) ◽  
pp. 40371-40382 ◽  
Author(s):  
Xuefei Leng ◽  
Zhiyong Wei ◽  
Yingying Ren ◽  
Yufei Bian ◽  
Qinyi Wang ◽  
...  
Keyword(s):  
Graft Copolymers ◽  
Controlled Synthesis ◽  
Side Chains ◽  
Trimethylene Carbonate

Synthesis of comb-like graft copolymers of lcP(LLA-co-TMC) from an organocatalyst/PB–OH system: including lcP(TMC-b-LLA), lcP(LLA-grad-TMC) and lcP(LLA-ran-TMC).

Poly[glycidyl oligo(oxyethylene)carbamate]s (PGn-EOmR’ and R-PGn-EOmR’): Controlled Synthesis and Effects of Molecular Parameters (n and m), Side Group (R’), and End-Group (R) on Thermoresponsive Property

2021 ◽  
Author(s):  
Tingyu He ◽  
Yanqiu Wang ◽  
Liang Xu ◽  
Xiangming Fu ◽  
Atsushi Narumi ◽  
...  
Keyword(s):  
Ring Opening ◽  
Glycidyl Ether ◽  
Controlled Synthesis ◽  
Side Chains ◽  
Side Group ◽  
Molecular Parameters ◽  
End Group

The controlled syntheses of glycerol-based polymers that consist of poly(glycidol) (PG)-backbones and thermoresponsive oligo(oxyethylene)-side chains are described. The organocatalytic ring-opening polymerizations of benzyl glycidyl ether (BnGE) were performed to produce...

Controlled Synthesis of Densely Grafted Bottlebrushes That Bear Helical Polyisocyanide Side Chains on Polyisocyanide Backbones and Exhibit Greatly Increased Viscosity

2020 ◽  
Vol 53 (8) ◽  
pp. 3224-3233 ◽  
Author(s):  
Yi-Xu Su ◽  
Lei Xu ◽  
Xun-Hui Xu ◽  
Xiao-Hua Hou ◽  
Na Liu ◽  
...  
Keyword(s):  
Controlled Synthesis ◽  
Side Chains
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