Synthesis of Bicyclic β‐Sultams

Cavagna, Friedrich; Koller, Wolfgang; Linkies, Adolf; Rehling, H.; Reuschling, D.

doi:10.1002/anie.198205482

Cited by 12 publications

(3 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Michael addition of glycine imines 30a and 30b was readily achieved using caesium carbonate in diisopropyl ether in conjunction with a quaternary ammonium catalyst. 28 Hydrolysis of the benzophenone imine, followed by basification 29 then led directly to the cyclic imines 35.…”

Section: Resultsmentioning

confidence: 99%

Stereocontrolled synthesis of lepadiformine A

2008

View full text Add to dashboard Cite

In this paper we present results of a study into whether the tricyclic core of the lepadiformines A-C can be accessed via intramolecular hetero-Diels-Alder cycloaddition. We are able to demonstrate that such a process is possible and that the reaction proceeds in an endo-selective fashion, providing the correct relative stereochemistry for this family of natural products. By employing this approach we have been able to develop a short (7 step) synthesis of (+/-)-lepadiformine A, starting from commercially-available trans-2-nonenal.

show abstract

Section: Resultsmentioning

confidence: 99%

Stereocontrolled synthesis of lepadiformine A

2008

View full text Add to dashboard Cite

show abstract

“…[35,36] Several variations of this synthetic scheme were described in the literature. [37] The strategy was also applied for the synthesis of other bicyclic β-sultams 18/19, [38] 20, [39] and 21. [40] Scheme 8.…”

Section: Fused β-Sultamsmentioning

confidence: 99%

Saturated Bicyclic Sultams

et al. 2020

View full text Add to dashboard Cite

Saturated bicyclic sultams represent a promising class of sp 3-rich three-dimensional scaffolds of outmost importance to organic and medicinal chemistry. In this review with 99 references, synthesis, properties, and applications of these compounds are surveyed. The literature data are categorized according to the structural types (i.e. fused, bridged, and spirocyclic compounds), as well as homologous series

show abstract

“…In initial reports31>32) we considered the possibility that the presence of a /Mactam ring was not mandatory for antibiotic activity but that a suitably activated amide bond was the major requirement. Twobicyclic y-lactams (10 and ll), racemic analogues of carbapenicillanic acid (12),33) were synthesised however they exhibited no antibacterial activity when tested against Bacillus subtilis ATCC6633 and Escherichia coli supersensitive strain No. 21/30 or /Mactamase inhibition against Bacillus cereus /Mactamase II and Klebsiella aerogenes BRL1003.…”

Section: Y-lactamsmentioning

confidence: 99%