39110-26-4Relevant articles and documents
Heavier Carbonyl Olefination: The Sila-Wittig Reaction
Reiter, Dominik,Frisch, Philipp,Szilvási, Tibor,Inoue, Shigeyoshi
supporting information, p. 16991 - 16996 (2019/10/16)
The Wittig reaction is one of the most versatile tools in the repertoire of organic chemists. Thus, a broad variety of carbonyl compounds can be converted to tailor-made alkenes with phosphorus ylides under mild conditions. However, no comparable reaction has been reported for silanones, the silicon congeners of ketones. Here, we demonstrate for the first time the successful application of the Wittig olefination to iminosilylsilanone 1. The selective formation of a series of silenes (R2Sia? CR2) via the sila-Wittig reaction revealed an unprecedented approach to otherwise elusive compounds. In addition, the highly reactive and zwitterionic nature of 1 was also susceptible to nucleophilic attacks and cycloaddition reactions by and with the phosphorus ylides. Our results therefore make another important contribution to discovering the differences and similarities between carbon and silicon.
Synthesis and biological evaluation of new cross-conjugated dienone marine prostanoid analogues
Kuhn, Cyrille,Roulland, Emmanuel,Madelmont, Jean-Claude,Monneret, Claude,Florent, Jean-Claude
, p. 2028 - 2039 (2007/10/03)
The synthesis of a series of brominated cross-conjugated dienones, marine prostanoid analogues, was considered using two cyclopentannelation processes, from enamine (by a domino 3-aza Claisen/Mannich reaction) and from dioxolane ester alkylation followed by intramolecular Wittig reaction. All the compounds synthesized featured the same cross-conjugated dienone system, with a vicinal syn or anti diol on the ω-chain. The replacement of the ω-side-chain of the natural prostanoids with a 1-hydroxyphenyl-butyl moiety gave new prostanoids (32-34) with good cytotoxicities. In a second series of products, the possibility of a shorter α-side-chain bearing a simple phenyl ester was investigated. The results indicated a dramatic increase in the cytotoxicity (39, 40, 43, 44). Finally, in a third series, the ω- 1-hydroxyphenyl-butyl was replaced by a 1-hydroxymethyloxybenzyl chain. These simpler compounds (45,46,47,48, 60) are still highly cytotoxic, in the medium range of 60 nM, close to the value of natural punaglandins.
Amide Bond Replacements Incorporated into CCK-B Selective "Dipeptoids"
Fincham, Christopher I.,Higginbottom, Michael,Hill, David R.,Horwell, David C.,O'Toole, John C,et al.
, p. 1472 - 1484 (2007/10/02)
This paper describes the chemical synthesis and CCK-B and CCK-A receptor binding affinities of a series of compounds in which the central amide bond of the CCK-B "dipeptoid" ligand tricyclo3,7>dec-2-yl-21-(hydroxymethyl)-2