Synthesis of novel ferrocene labelled steroidal derivatives via palladium-catalysed carbonylation. X-ray structure of 17-(N-(4′-((2-ferrocenyl-ethenyl)-carbonyl)-phenyl)carbamoyl)-5α-androst-16-ene

Synthesis of new steroid-β-lactam hybrids via palladium-catalyzed aminocarbonylation

“…According to our own previous results, good yields can be obtained in the presence of a twofold excess of the nucleophiles, even with less nucleophilic primary amines, such as amino acid esters [23]. Moreover, in the carbonylation of steroids with ferrocenyl chalcones, optimal results were achieved using a slight excess of the steroidal substrates [24].…”

“…In the past few years, palladium-catalyzed aminocarbonylation of aryl or alkenyl halides has been investigated in our group using a great variety of nucleophilic reagents, such as primary and secondary amines [18] ammonium carbamate [19], hydrazines [20], amino acids [21e23] and ferrocenyl chalcones [24]. Mild reaction conditions and high selectivity rendered this reaction a very useful tool for the functionalization of steroidal 17-iodo-16-enes ( Fig.…”

“…Mild reaction conditions and high selectivity rendered this reaction a very useful tool for the functionalization of steroidal 17-iodo-16-enes ( Fig. 1) bearing different moieties in rings A and B [19,20,23,24]. The products were obtained in excellent yields so we decided to use this methodology to synthesize the new steroid-b-lactam hybrids.…”

“…Reaction conditions for palladium-catalyzed carbonylation were chosen according to our previous observations concerning similar reactions of steroidal substrates [19,20,23,24]. Carbonylations were carried out in the presence of the Pd(OAc) 2 e triphenylphosphane system, the catalytically active Pd(0) complex was formed in situ from the palladium salt and the phosphane [31].…”

Palladium-catalyzed reaction of 2-iodoferrocenyl alcohols with internal alkynes: Synthesis of functionally 1,2-disubstituted ferrocenes and ferroceno-pyrans

“…The cytotoxic efficacy of ferrocenesubstituted hydroxytamoxifen analogs, hydroxyferrocifens, have been explained via a proton-coupled electron transfer mechanism involving the redox states (Fe 2þ /Fe 3þ ) of the iron atom [53]. In addition, numerous ferrocene-containing biomolecules such as amino acids [35,54e57], peptides [35,58e62] proteins [63e66], nucleobases [35,67], steroids [68,69] and lipids [70e72] have been prepared and these bioconjugates of ferrocene were generally used as electrochemical sensors in biological applications. Therefore, the synthesis of new functionalized ferrocenes and ferrocenylsubstituted carbo-and heterocyclic structures are currently receiving considerable attention.…”