63559-15-9Relevant academic research and scientific papers
A Negishi cross-coupling reaction enables the total synthesis of (+)-stachyflin
Haut, Franz-Lucas,Speck, Klaus,Wildermuth, Raphael,M?ller, Kristof,Mayer, Peter,Magauer, Thomas
, p. 3348 - 3357 (2018/03/06)
We present a full account on the development of the total synthesis of the antiviral meroterpenoid (+)-stachyflin. The decalin subunit is rapidly accessed by an exo-selective Diels–Alder reaction, whereas the isonindolinone was synthesized via a highly efficient and practical de novo route starting from dimedone. A challenging sp2–sp3 Negishi cross-coupling reaction enabled construction of the crucial C15–C16 bond that connects the arene with the decalin subunit. For the final installation of the cis-decalin framework, a Lewis acid-catalyzed cyclization was applied.
Practical synthesis of a functionalized 1-oxo-1,2,3,4- tetrahydroisoquinoline-3-carboxylic acid
Quintiliano, Samir A.P.,Silva Jr., Luiz F.
scheme or table, p. 3808 - 3810 (2012/09/22)
The synthesis of a functionalized 1-oxo-1,2,3,4-tetrahydroisoquinoline-3- carboxylic acid has been performed in 10 steps from the readily available dimedone. Only three purifications by flash chromatography are required through the whole sequence. The key step is the reaction between a dimedone derivative and a chlorotetrolic ester, that gives a tetrasubstituted benzene ring (through a Diels-Alder/retro- Diels-Alder process) bearing the substituents in the suitable positions for further functionalization.
Domino reaction of 1,3-bis(trimethylsilyloxy)-1,3-dienes with oxalyl chloride: General and stereoselective synthesis of γ-alkylidenebutenolides
Langer, Peter,Schneider, Toni,Stoll, Martin
, p. 3204 - 3214 (2007/10/03)
The Lewis acid catalyzed cyclization of oxalyl chloride with 1,3-bis-(trimethylsilyloxy)-1,3-dienes 3, derived from 1,3-dicarbonyl compounds 1, provides a new and general approach for the synthesis of γ-alkylidenebutenolides 4, a pharmacologically and syn
