3206-49-3Relevant academic research and scientific papers
Practical synthesis of β-carbonyl phenyltetrazolesulfones and investigations of their reactivities in organocatalysis
Zweifel, Theo,Nielsen, Martin,Overgaard, Jacob,Jacobsen, Christian Borch,Jorgensen, Karl Anker
supporting information; experimental part, p. 47 - 52 (2011/03/18)
A practical synthesis of β-carbonyl phenyltetrazolesulfones, useful for a series of enantioselective reactions, is shown. Aryl, alkyl and ester carbonyl compounds all proved to be efficiently synthesised, leading to products in up to >99% yield over two s
Total synthesis of (+)-amphidinolide A. Assembly of the fragments
Trost, Barry M.,Wrobleski, Stephen T.,Chisholm, John D.,Harrington, Paul E.,Jung, Michael
, p. 13589 - 13597 (2007/10/03)
The structure elucidation of (+)-amphidinolide A, a cytotoxic macrolide, has been accomplished by employing a combination of total synthesis and NMR spectroscopic analysis. Amphidinolide A possesses two skipped 1,4-diene subunits which are accessible by ruthenium-catalyzed alkene-alkyne couplings. Previous total syntheses had revealed that the reported structure was incorrect; therefore, to incorporate maximum flexibility into the synthesis, with the ultimate goal of determining the correct structure, a highly convergent approach was chosen. Furthermore, liberal use was made of catalytic asymmetric transformations to set individual stereocenters. Three different strategies were envisioned for the end game, and due to the highly convergent nature of the synthesis, all three routes disconnect to the same three key intermediates, 5, 6, and 7. Diastereomers of 6 and 7 were easily prepared by modification of the synthetic routes to allow access to multiple diastereomers of 1 for structural determination.
Ruthenium-catalyzed alkene-alkyne coupling: Synthesis of the proposed structure of amphidinolide A
Trost, Barry M.,Chisholm, John D.,Wrobleski, Stephen T.,Jung, Michael
, p. 12420 - 12421 (2007/10/03)
The ruthenium-catalyzed alkene-alkyne coupling provides a powerful method for the synthesis of 1,4 dienes and a way to simplify synthetic strategy. The latter potential is explored in the context of a synthesis of the assigned structure of amphidinolide A
ANTIMYCOBACTERIAL DERIVATIVES OF TETRAZOLE
Waisser, Karel,Vanzura, Jiri,Hrabalek, Alexandr,Vinsova, Jarmila,Gresak, Stefan,et al.
, p. 2389 - 2394 (2007/10/02)
A synthesis of (1-phenyltetrazol-5-ylthio)acetic acid derivatives has been developed.Functional variations concern the carboxylic group and/or the 4 position of phenyl group.Most of the compounds prepared have been tested with regard to their antimycobact
