39616-20-1Relevant academic research and scientific papers
Remote Nucleophilic Allylation by Allylrhodium Chain Walking
Groves, Alistair,Martínez, Jose I.,Smith, Joshua J.,Lam, Hon Wai
supporting information, p. 13432 - 13436 (2018/09/21)
Metal migration through a carbon chain is a versatile method for achieving remote functionalization. However, almost all known examples involve the overall net migration of alkylmetal species. Here, we report that allylrhodium species obtained from hydrorhodation of 1,3-dienes undergo chain walking toward esters, amides, or (hetero)arenes over distances of up to eight methylene units. The final, more highly conjugated allylrhodium species undergo nucleophilic allylation with aldehydes and with an imine to give Z-homoallylic alcohols and amines, respectively.
Streptopyridines, volatile pyridine alkaloids produced by Streptomyces sp. FORM5
Groenhagen, Ulrike,Maczka, Michael,Dickschat, Jeroen S.,Schulz, Stefan
, p. 1421 - 1432 (2014/07/22)
Streptomyces sp. FORM5 is a bacterium that is known to produce the antibiotic streptazolin and related compounds. We investigated the strain for the production of volatiles using the CLSA (closed-loop stripping analysis) method. Liquid and agar plate cultures revealed the formation of new 2-alkylpyridines (streptopyridines), structurally closely related to the already known 2-pentadienylpiperidines. The structures of the streptopyridines A to E were confirmed by total synthesis. The analysis of the liquid phase by solvent extraction or extraction with an Oasis adsorbent showed that streptazolin and 2-pentadienylpiperidine are the major compounds, while the streptopyridines are only minor components. In the gas phase, only the streptopyridines could be detected. Therefore, an orthogonal set of analysis is needed to assess the metabolic profile of bacteria, because volatile compounds are obviously overlooked by traditional analytical methods. The streptopyridines are strain specific volatiles that are accompanied by a broad range of headspace constituents that occur in many actinomycetes. Volatiles might be of ecological importance for the producing organism, and, as biosynthetic intermediates or shunt products, they can be useful as indicators of antibiotic production in a bacterium.
Synthesis of 1-Acyl-2-alkylcyclopropanecarboxylic Esters from 2-Alkenylphosphonium Salts
Jacoby, D.,Celerier, J. P.,Petit, H.,Lhommet, G.
, p. 301 - 304 (2007/10/02)
The one-pot reaction of allyltriphenylphosphonium bromide with the sodium salts of β-keto esters leads to the formation of alkyl 1-acyl-2-alkylcyclopropanecarboxylates.
