153974-48-2Relevant academic research and scientific papers
Palladium-Catalyzed Carbonylative Cyclization of o-Allylbenzyl Halides To Produce Benzo-Annulated Enol Lactones and/or Bicyclohept-3-en-6-ones. An Efficient Route to U-68,215
Wu, Guangzhong,Shimoyama, Izumi,Negishi, Ei-ichi
, p. 6506 - 6507 (1991)
Treatment of o-allylbenzyl halides with CO in the presence of 1.5-2.0 equiv of a base, such as NEt3, and a catalytic amount of a palladium complex, such as Cl2Pd(PPh3)2, provides a 2,3,3a,4-tetrahydro-2-oxonaphthylfurans and/or cyclobutanone derivatives tentatively identified as 2,2a,7,7a-tetrahydro-1H-cyclobutinden-2-ones.
AMINE SALTS OF A PROSTACYCLIN ANALOG
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Paragraph 0331; 0332, (2015/06/03)
The present invention provides amine salts of the prostacyclin analogue of Formula I and processes for generating these amine salts.
METHODS OF SYNTHESIZING A PROSTACYCLIN ANALOG
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Paragraph 90-91, (2014/06/24)
The present invention provides processes for preparing a prostacyclin analogue of Formula (I) or a pharmaceutically acceptable salt thereof, wherein R10 is a linear or branched C1-6 alkyl. The processes of the present invention comprise steps that generate improved yields and fewer byproducts than traditional methods. The processes of the present invention employ reagents (e.g., the oxidizing reagent) that are less toxic that those used in the traditional methods (e.g., oxalyl chloride). Many of the processes of the present invention generate intermediates with improved e.e. and chemical purity; thereby eliminating the need of additional chromatography steps. And, the processes of the present invention are scalable to generate commercial quantities of the final compound.
The Intramolecular Asymmetric Pauson-Khand Cyclization As A Novel and General Stereoselective Route to Benzindene Prostacyclins: Synthesis of UT-15 (Treprostinil)
Moriarty, Robert M.,Rani, Neena,Enache, Livia A.,Rao, Munagala S.,Batra, Hitesh,Guo, Liang,Penmasta, Raju A.,Staszewski, James P.,Tuladhar, Sudersan M.,Prakash, Om,Crich, David,Hirtopeanu, Anca,Gilardi, Richard
, p. 1890 - 1902 (2007/10/03)
A general and novel solution to the synthesis of biologically important stable analogues of prostacyclin PGI2, namely benzindene prostacyclins, has been achieved via the stereoselective intramolecular Pauson-Khand cyclization (PKC). This work illustrates for the first time the synthetic utility and reliability of the asymmetric PKC route for synthesis and subsequent manufacture of a complex drug substance on a multikilogram scale. The synthetic route surmounts issues of individual step stereoselectivity and scalability. The key step in the synthesis involves efficient stereoselection effected in the PKC of a benzoenyne under the agency of the benzylic OTBDMS group, which serves as a temporary stereodirecting group that is conveniently removed via benzylic hydrogenolysis concomitantly with the catalytic hydrogenation of the enone PKC product. Thus the benzylic chiral center dictates the subsequent stereochemistry of the stereogenic centers at three carbon atoms (C3a, C9a, and C1).
Palladium-catalyzed carbonylative cyclization via trapping of acylpalladium derivatives with internal enolates. Its scope and factors affecting the C-to-O ratio
Negishi, El-Ichi,Coperet, Christophe,Sugihara, Takumichi,Shimoyama, Izumi,Zhang, Yantao,Wu, Guangzhong,Tour, James M.
, p. 425 - 436 (2007/10/02)
The Pd-catalyzed carbonylative cyclization reaction involving ω-acyl-substituted acylpalladium derivatives can proceed via intramolecular trapping with either C- or O-enolates; the preferential formation of either 5- or 6-membered rings dictates the C-to-
