Synthesis of (±)-ramulosin via inverse type hetero-diels-alder reaction 1

Vogt, K.; Schmidt, Richard R.

doi:10.1016/s0040-4020(01)85960-3

Cited by 13 publications

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Dihydropyrans by Cycloadditions of Oxadienes

et al. 2020

View full text Add to dashboard Cite

3,4‐Dihydro‐2H‐pyrans are present in the skeletons of several natural products, and these versatile synthetic intermediates are readily transformed into tetrahydropyrans, pyridines, or 1,5‐dicarbonyl units. Among the strategies developed to access 3,4‐dihydro‐2H‐pyrans, the hetero‐Diels‐Alder reaction between an oxadiene and a dienophile is particularly valuable because up to three contiguous stereogenic centers can be created diastereo‐ and/or enantioselectively in a single step. This review addresses the mechanism of the reaction and presents methods for preparing the product dihydropyrans enantio‐ and diastereoselectively. Thermal and Lewis acid promoted cycloadditions are discussed, as is the role of activating groups on the oxadiene.

show abstract

Dihydropyrans by Cycloadditions of Oxadienes

et al. 2020

View full text Add to dashboard Cite

show abstract

Synthese und pharmakologische Eigenschaften eines neuartigen herzwirksamen Steroids

et al. 1989

View full text Add to dashboard Cite

Wie greifen herzaktive Steroidlactone in das molekulare Geschehen ein? Man weiß, daß sie die Na⊕/K⊕‐ATPase hemmen, ein Enzym, das den aktiven Transport von Na⊕ und K⊕ durch die Plasmamembran tierischer Zellen bewirkt. Um festzustellen, wo das Enzym die Steroidlactone bindet, wurde ein flexibler Syntheseweg für Verbindungen des Typs 1 entwickelt. Angestrebt werden Substanzen mit einer reaktiven Gruppe R. Die Stammverbindung 1, R = H, hemmt die Na⊕/K⊕‐ATPase und ist positiv inotrop wirksam.

show abstract

Synthesis and Pharmacological Properties of a Novel Cardioactive Steroid

Werner

Möller

Wagner

et al. 1989

Angew. Chem. Int. Ed. Engl.

View full text Add to dashboard Cite

How do cardioactive steroid lactones exert their effects? It is known that they inhibit Na⊕/K⊕ ATPase, an enzyme that serves in the active transport of Na⊕ and K⊕ across the plasma membrane. To determine where the steroid lactones bind on the enzyme, a flexible synthetic route to compounds of type 1 was developed. The goal was to obtain substances containing a reactive R group. The parent compound 1, R  H, inhibits the Na⊕/K⊕ ATPase and exerts a positive inotropic effect.

show abstract

Synthesis of (±)-ramulosin via inverse type hetero-diels-alder reaction 1

Cited by 13 publications

References 42 publications

Dihydropyrans by Cycloadditions of Oxadienes

Dihydropyrans by Cycloadditions of Oxadienes

Synthese und pharmakologische Eigenschaften eines neuartigen herzwirksamen Steroids

Synthesis and Pharmacological Properties of a Novel Cardioactive Steroid

Contact Info

Product

Resources

About