ChemInform Abstract: A New Approach Toward the Stereoselective Synthesis of Novel Quinolyl Glycines: Synthesis of the Enantiomerically Pure Quinolyl-β-Amino Alcohol Precursors.

ChemInform ◽  
2010 ◽  
Vol 31 (34) ◽  
pp. no-no
Author(s):  
Gemma Cabarrocas ◽  
Sara Rafel ◽  
Montserrat Ventura ◽  
Jose M. Villalgordo
Keyword(s):  
Amino Alcohol ◽  
Stereoselective Synthesis ◽  
New Approach ◽  
Enantiomerically Pure

Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis

2015 ◽  
Vol 54 (46) ◽  
pp. 13764-13768 ◽  
Author(s):  
Wilko Greschner ◽  
Beate Neumann ◽  
Hans-Georg Stammler ◽  
Harald Gröger ◽  
Dietmar Kuck
Keyword(s):  
Stereoselective Synthesis ◽  
Enantiomerically Pure

Direct Stereoselective Synthesis of Enantiomerically Pure anti-β-Amino Alcohols

2014 ◽  
Vol 79 (15) ◽  
pp. 6775-6782 ◽  
Author(s):  
Gastón Silveira-Dorta ◽  
Osvaldo J. Donadel ◽  
Víctor S. Martín ◽  
José M. Padrón
Keyword(s):  
Stereoselective Synthesis ◽  
Amino Alcohols ◽  
Enantiomerically Pure

Enantioselective synthesis of 1-aryl-2-propenylamines: a new approach to a stereoselective synthesis of the Taxol® side chain

2004 ◽  
Vol 15 (6) ◽  
pp. 941-949 ◽  
Author(s):  
Daniele Castagnolo ◽  
Silvia Armaroli ◽  
Federico Corelli ◽  
Maurizio Botta
Keyword(s):  
Stereoselective Synthesis ◽  
Enantioselective Synthesis ◽  
Side Chain ◽  
New Approach

A new approach to the stereoselective synthesis of trans-3-carbamoyl-β-lactam moieties

2017 ◽  
Vol 41 (6) ◽  
pp. 2479-2489 ◽  
Author(s):  
Anna Zakaszewska ◽  
Ewelina Najda-Mocarska ◽  
Sławomir Makowiec
Keyword(s):  
Stereoselective Synthesis ◽  
Optically Active ◽  
Thermal Generation ◽  
New Approach

Optically active 1,4-disubstituted-3-carbamoyl-azetidinones are synthesized from 5-[(N-arylamino)(hydroxyl)methylene]-2,2-dimethyl-1,3-dioxa-4,6-diones and chiral aldimines via thermal generation of carbamoyl ketenes and subsequent [2+2] cycloaddition.

A new approach to the stereoselective synthesis of C-nucleosides via homolytic heteroaromatic substitution

1992 ◽  
Vol 33 (49) ◽  
pp. 7575-7578 ◽  
Author(s):  
Elena Vismara ◽  
Giangiacomo Torri ◽  
Nadia Pastori ◽  
Marco Marchiandi
Keyword(s):  
Stereoselective Synthesis ◽  
New Approach

Stereoselective Synthesis of Enantiomerically Pure Piperidine Derivatives by N-Galactosylation of Pyridones.

ChemInform ◽  
2004 ◽  
Vol 35 (46) ◽  
Author(s):  
Ellen Klegraf ◽  
Markus Follmann ◽  
Dieter Schollmeyer ◽  
Horst Kunz
Keyword(s):  
Stereoselective Synthesis ◽  
Enantiomerically Pure

The Fürstner Synthesis of Amphidinolide F

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Amino Alcohol ◽  
Aldol Condensation ◽  
Free Acid ◽  
The Other ◽  
Unsaturated Ester ◽  
Alkyne Metathesis ◽  
Max Planck ◽  
Ring Closing Metathesis ◽  
Enantiomerically Pure ◽  
Metathesis Catalyst

The amphidinolides, having zero, one, or (as exemplified by amphidinolide F 3) two tetrahydrofuran rings, have shown interesting antineoplastic activity. It is a tribute to his development of robust Mo catalysts for alkyne metathesis that Alois Fürstner of the Max-Planck-Institut für Kohlenforschung Mülheim could with confidence design (Angew. Chem. Int. Ed. 2013, 52, 9534) a route to 3 that relied on the ring-closing metathesis of 1 to 2 very late in the synthesis. Three components were prepared for the assembly of 1. Julia had already reported (J. Organomet. Chem. 1989, 379, 201) the preparation of the E bromodiene 5 from the sulfone 4. The alcohol 7 was available by the opening of the enantiomerically-pure epoxide 6 with propynyl lithium, followed by oxidation following the Pagenkopf pro­tocol. Amino alcohol-directed addition of the organozinc derived from 5 to the alde­hyde from oxidation of 7 completed the assembly of 8. Addition of the enantiomer 10 of the Marshall butynyl reagent to 9 followed by protection, oxidation to 11, and addition of, conveniently, the other Marshall enan­tiomer 12 led to the protected diol 13. Silylcupration–methylation of the free alkyne set the stage for selective desilylation and methylation of the other alkyne. Iodination then completed the trisubstituted alkene of 14. Methylation of the crystalline lactone 15, readily prepared from D-glutamic acid, led to a mixture of diastereomers. Deprotonation of that product followed by an aque­ous quench delivered 16. Reduction followed by reaction with the phosphorane 17 gave the unsaturated ester, that cyclized with TBAF to the crystalline 18. The last ste­reogenic center of 22 was established by proline-mediated aldol condensation of the aldehyde 19 with the ketone 20. To assemble the three fragments, the ketone of 21 was converted to the enol triflate and thence to the alkenyl stannane. Saponification gave the free acid 22, that was acti­vated, then esterified with the alcohol 18. Coupling of the stannane with the iodide 14 followed by removal of the TES group led to the desired diyne 1. It is noteworthy that the Mo metathesis catalyst is stable enough to tolerate the free alcohol of 1 in the cyclization to 2.

Stereoselective Synthesis of Quinolizidine Alkaloids: (–)-Lasubin II

2008 ◽  
Vol 63 (4) ◽  
pp. 425-430 ◽  
Author(s):  
Markus Weymann ◽  
Horst Kunz
Keyword(s):  
Mannich Reaction ◽  
Stereoselective Synthesis ◽  
Pure Form ◽  
Quinolizidine Alkaloids ◽  
Enantiomerically Pure ◽  
Quinolizidine Alkaloid

AbstractBased on a higly diastereoselective Mannich reaction of N-(3,4-dimethoxybenzylidene) 2,3,4,6- tetra-O-pivaloyl-β -D-galactopyranosylamine 3 with the Danishefsky diene the quinolizidine alkaloid lasubin II was synthesized in enantiomerically pure form in six steps.

Stereoselective synthesis and characterization of new enantiomerically pure phosphoric acids

Chirality ◽  
2009 ◽  
pp. NA-NA
Author(s):  
Cinzia Biaggi ◽  
Maurizio Benaglia ◽  
Rita Annunziata ◽  
Sergio Rossi
Keyword(s):  
Stereoselective Synthesis ◽  
Synthesis And Characterization ◽  
Enantiomerically Pure ◽  
Phosphoric Acids
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