286440-96-8Relevant academic research and scientific papers
Synthesis of Aminoallenes via Selenium-π-Acid-Catalyzed Cross-Coupling of N-Fluorinated Sulfonimides with Simple Alkynes
Rode, Katharina,Ramadas Narasimhamurthy, Poorva,Rieger, Rene,Kr?tzschmar, Felix,Breder, Alexander
, p. 1720 - 1725 (2021/03/16)
The facile synthesis of aminoallenes, accomplished by a selenium-π-acid-catalyzed cross-coupling of an N-fluorinated sulfonimide with simple, non-activated alkynes, is reported. Until now, aminoallenes were difficult to be accessed by customary means, inasmuch as pre-activated and, in part, intricate starting materials were necessary for their synthesis. In sharp contrast, the current study shows that ordinary internal alkynes can serve as simple and readily available precursors for the construction of the aminoallene motif. The operating reaction conditions tolerate numerous functional groups such as esters, nitriles, (silyl)ethers, acetals, and halogen substituents, furnishing the target compounds in up to 86 % yield.
Toward Leiodermatolide: Synthesis of the Core Structure
Reiss, Anita,Maier, Martin E.
supporting information, p. 3146 - 3149 (2016/07/13)
The macrocyclic core (35) of the marine natural product leiodermatolide (1) was synthesized from two key fragments, vinyl iodide 23 (C1-C11 part) and vinyl stannane 31 (C12-C18 part). A Stille coupling led to conjugated Z,Z-diene 32. The derived seco acid 34 was cyclized using a Yamaguchi macrolactonization. Key steps in the assembly of vinyl iodide 23 were a Paterson aldol reaction, and a Kumada coupling on a triflate derivative to create the C4-C5 trisubstituted double bond. The two stereocenters in fragment 31 were established by a Marshall-Tamaru reaction. The longest linear sequence comprises 20 steps.
Synthesis of polyisoprene terpenoid dendrons and their applications in oligo(phenylene ethynylene)s as "shells"
Chai, Wen-Yu,Shi, Zi-Fa,An, Peng,Wang, Wei,Wang, Lu-Feng,Cao, Xiao-Ping
supporting information; experimental part, p. 143 - 155 (2012/03/26)
The novel double-stage convergent synthesis of a new class of polyisoprene terpenoid (PIPTP) dendrons is described. PIPTP dendrons bear a highly branched aliphatic hydrocarbon skeleton and a hydrophilic hydroxy focal point functionality. These dendrons have the specific formula C (5×2G+1-5)H(5×2 G+2-8)O, and each dendritic layer is constructed from an isoprene unit. The key branching steps involve a double alkyl-metal addition to an ester functionality, followed by deoxygenation of the resulting tertiary alcohol by triethylsilane and trifluoroacetic acid, then hydrogenation or hydrogenolysis. The dendrons were also attached to oligo(phenylene ethynylene)s (OPEs) so as to function as protective shells to allow fine tuning of the nanoscopic environment around the OPE moiety, and to exert precise control of the packing density and intermolecular interaction between the OPE cores. Fluorescence quantum yield data reveal that the OPE core is better encapsulated by the PIPTP dendrons than by Frechet dendrons.
Novel synthesis of amphiphilic dendrons by the double-stage convergent method
Shi, Zi-Fa,Chai, Wen-Yu,An, Peng,Cao, Xiao-Ping
supporting information; experimental part, p. 4394 - 4397 (2009/12/26)
A serles of amphophilic dendrons (G1-G4) have been designed and synthesized, which have a highly branched aliphatic hydrocarbon skeleton and a hydrophilic hydroxyl functionality to enable conjugation with other substrates. The higher generation dendrons (G3 and G4) were synthesized by a double-stage convergent method, which shortened the synthetic route significantly and provided the products In an efficient manner. The key branching step involved a double alkyl-metal addition to an ester functionality followed by deoxygenation of a resulting tertiary alcohol by triethylsilane.
AMIDE DERIVATIVES
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Page/Page column 133; 134, (2008/06/13)
The invention concerns amide compounds of Formula (I) wherein groups R1, R2, R3, Q1, X, R4, R5, R6, and R7 are as defined in the description. The present invention als
METHOD FOR PRODUCING PROSTAGLANDIN DERIVATIVE, PROSTAGLANDIN DERIVATIVE, INTERMEDIATE COMPOUND THEREFOR AND METHOD FOR PRODUCING THE SAME
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Page/Page column 24, (2010/02/15)
PROBLEM TO BE SOLVED: To provide a method for producing a prostaglandin derivative, the prostaglandin derivative and an intermediate compound therefor, especially a method for producing a δ-12-prostaglandin J2 derivative using a new method for chemical synthesis through the intermediate compound. SOLUTION: The method for production is a method for producing the prostaglandin derivative using (1R,3R)-4-cyclopentene-1,3-diol 3-acetate (carboxylate) as a starting material. The method is composed of (A) an α-side chain introduction step of providing a malonic acid ester addition compound at the 3-position of the (1R,3R)-4-cyclopentene-1,3-diol, (B) an α-side chain extension step of affording a (1R,3R)-4-cyclopenten-1-one compound having the α-side chain of the prostaglandin derivative at the 3-position and (C) a prostaglandin derivative synthesizing step of conversion into the prostaglandin derivative.
