114413-26-2Relevant articles and documents
Total synthesis of clavaminol A, C and H
Zaed, Ahmed M.,Sutherland, Andrew
, p. 8030 - 8037 (2011)
The first total synthesis of clavaminol A and C, (2R,3S)-2-amino-3-alkanols from the Mediterranean ascidian Clavelina phlegraea has been achieved in 29% overall yield. The key step involved a palladium(ii)-catalysed directed Overman rearrangement to create the C-N bond and install the erythro configuration while a one-pot, tributyltin hydride-mediated reduction allowed simultaneous formation of the methyl side-chain and N-acetyl group. Similarly, the first total synthesis of clavaminol H was completed in 48% overall yield using an approach that also provided the cytotoxic des-acetyl analogue. The Royal Society of Chemistry 2011.
Epoxidation of olefins with peracid at low temperature with copper catalysis
Andrus, Merritt B.,Poehlein, Benjamin W.
, p. 1013 - 1014 (2000)
Treatment of a wide range of olefins with m-chloroperbenzoic acid (MCPBA) at low temperature in the presence of copper(I) and (II) catalysts in methylene chloride provides epoxides in good to excellent yields. (C) 2000 Elsevier Science Ltd.
A versatile route to polythiophenes with functional pendant groups using alkyne chemistry
Huang, Xiao,Yang, Li,Emanuelsson, Rikard,Bergquist, Jonas,Str?mme, Maria,Sj?din, Martin,Gogoll, Adolf
, p. 2682 - 2688 (2016)
A new versatile polythiophene building block, 3-(3,4-ethylenedioxythiophene)prop-1-yne (pyEDOT) (3), is prepared from glycidol in four steps in 28% overall yield. pyEDOT features an ethynyl group on its ethylenedioxy bridge, allowing further functionalization by alkyne chemistry. Its usefulness is demonstrated by a series of functionalized polythiophene derivatives that were obtained by pre- and post-electropolymerization transformations, provided by the synthetic ease of the Sonogashira coupling and click chemistry.
Total Synthesis of (?)-Histrionicotoxin through a Stereoselective Radical Translocation–Cyclization Reaction
Sato, Manabu,Azuma, Hiroki,Daigaku, Akihiro,Sato, Sota,Takasu, Kiyosei,Okano, Kentaro,Tokuyama, Hidetoshi
, p. 1087 - 1091 (2017)
Stereoselective total syntheses of (?)-histrionicotoxin and (?)-histrionicotoxin 235A are described. The 1-azaspiro[5.5]undecane skeleton was constructed diastereoselectively by a radical translocation–cyclization reaction involving a chiral cyclic acetal; the use of tris(trimethylsilyl)silane was crucial for the high diastereoselectivity. The cyclization product was converted into (?)-histrionicotoxin 235A through a one-pot partial-reduction–allylation reaction of a derivative containing an unprotected lactam. Finally, two terminal alkenes were transformed into enynes with the 1,3-amino alcohol protected as an oxathiazolidine oxide to complete the total synthesis of (?)-histrionicotoxin.
Studies toward the Synthesis of an Oxazole-Based Analog of (-)-Zampanolide
Bold, Christian P.,Klaus, Cindy,Pfeiffer, Bernhard,Schurmann, Jasmine,Lombardi, Rafael,Lucena-Agell, Daniel,Diaz, J. Fernando,Altmann, Karl-Heinz
, p. 2238 - 2242 (2021/04/05)
Studies are described toward the synthesis of an oxazole-based analog of (-)-zampanolide (2). Construction of (-)-dactylolide analog 22 was achieved via alcohol 5 and acid 4 through esterification and Horner-Wadsworth-Emmons (HWE)-based macrocyclization; however, attempts to attach (Z,E)-sorbamide to 22 proved unsuccessful. The C(8)-C(9) double bond of the macrocycle was prone to migration into conjugation with the oxazole ring, which may generally limit the usefulness of zampanolide analogs with aromatic moieties as tetrahydropyran replacements.
Synthesis method of glycerol carbonate
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Paragraph 0041; 0042; 0043, (2017/10/13)
The invention relates to the field of glycerol carbonate, particularly a synthesis method of high-purity glycerol carbonate. According to the method, glycidol is utilized to prepare the high-purity glycerol carbonate. The method comprises the following steps: adding glycidol, triethylamine and dichloromethane into a reaction kettle, performing cooling to 0 DEG C, dropwisely adding a silyl protecting group, recovering to room temperature after the dropwise addition is finished, performing reaction over night, performing washing with water, drying and distillation to obtain silyl-protected glycidol, performing addition reaction with carbon dioxide by using a catalyst to obtain silyl-protected glycerol carbonate, performing deprotection by using an acid, and performing distillation to remove the solvent, thereby obtaining the high-purity glycerol carbonate. The method has the advantages of simple technical operation process, recyclable raw materials, high product purity and low hazard, and is suitable for industrial production.