126696-08-0Relevant articles and documents
Total Synthesis and Structure Revision of a Fungal Glycolipid Fusaroside
Jana, Santanu,Sarpe, Vikram A.,Kulkarni, Suvarn S.
, p. 1664 - 1668 (2021)
Herein, we report a strategy for the total synthesis of a structurally unique fungal glycolipid fusaroside. The first total synthesis of the proposed structure involved construction of the complex, branched lipid chain having a variety of alkenes with E stereochemistry and attachment of the masked α,β-unsaturated β-keto acid at the O-4 position of trehalose as key steps. We propose a revision in the structure of fusaroside, particularly the position of olefins in the lipid chain.
Oxygenated N-Acyl Alanine Methyl Esters (NAMEs) from the Marine Bacterium Roseovarius tolerans EL-164
Bruns, Hilke,Herrmann, Jennifer,Müller, Rolf,Wang, Hui,Wagner D?bler, Irene,Schulz, Stefan
, p. 131 - 139 (2018)
The marine bacterium Roseovarius tolerans EL-164 (Rhodobacteraceae) can produce unique N-acylalanine methyl esters (NAMEs) besides strucutrally related N-acylhomoserine lactones (AHLs), bacterial signaling compounds widespread in the Rhodobacteraceae. The structures of two unprecedented NAMEs carrying a rare terminally oxidized acyl chain are reported here. The compounds (Z)-N-16-hydroxyhexadec-9-enoyl-l-alanine methyl ester (Z9-16-OH-C16:1-NAME, 3) and (Z)-N-15-carboxypentadec-9-enoyl-l-alanine methyl ester (16COOH-C16:1-NAME, 4) were isolated, and the structures were determined by NMR and MS experiments. Both compounds were synthesized to prove assignments and to test their biological activity. Finally, non-natural, structurally related Z9-3-OH-C16:1-NAME (18) was synthesized to investigate the mass spectroscopy of structurally related NAMEs. Compound 3 showed moderate antibacterial activity against microorganisms such as Bacillus, Streptococcus, Micrococcus, or Mucor strains. In contrast to AHLs, quorum-sensing or quorum-quenching activity was not observed.
Total Synthesis of Resolvin T4
Arai, Kohei,Kobayashi, Yuichi,Ogawa, Narihito
supporting information, p. 76 - 79 (2021/11/30)
A total synthesis of resolvin T4 was achieved by connecting three intermediates by Wittig reactions. The enal in the C1 C10 part was constructed through reduction of a propargylic alcohol with Red-Al followed by oxidation. The enal moiety in the C11 C16 part was synthesized by a ring-opening reaction of a silyl epoxide followed by a Peterson elimination. The chiral centers at C7 and C13 were constructed by ruthenium-catalyzed asymmetric transfer hydrogenation.
Red-light-mediated BartonMcCombie reaction
Ichii, Naoki,Ogura, Akihiro,Shibata, Kouhei,Takao, Ken-Ichi
supporting information, p. 936 - 941 (2020/11/09)
A red-light-mediated BartonMcCombie reaction is described, in which chlorophyll a is used as a photocatalyst and tris(trimethylsilyl)silane or Hantzsch ester is used as the hydrogen source. The reaction can be performed with a set of easily available equipment and reagents, and a variety of linear and cyclic xanthates could be applied. In contrast to the traditional conditions, the reaction does not involve toxic organotin or an explosive radical initiator. The reaction mechanism was analyzed both by experiments and computation, and it was suggested that the radical chain mechanism initiated by excitation of complex followed by charge transfer is likely to be operative.
