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.
Radical cyclization using a thioacetal group for radical generation
Nishida, Atsushi,Kawahara, Norio,Nishida, Mayumi,Yonemitsu, Osamu
, p. 9713 - 9734 (1996)
The generation and cyclization of several heterocyclic radicals were investigated. The hydrogen abstraction from 1,3-dithiane, 1,3-dithiolane, and 1,3-oxathiane rings by a benzophenone triplet generated the corresponding heterocyclic radicals, which gave the cyclized products by intramolecular addition to α,β-unsaturated esters. Diastereoselective radical cyclization using chiral acetals was also investigated.
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.
Formation of isomerized E,Z-configured 1,3-dienes in construction of macrocyclic trienes by diene-ene RCM
Takagi, Ryukichi,Tanaka, Kenji,Yamamoto, Koumei,Hiraga, Yoshikazu,Kojima, Satoshi,Abe, Manabu
, p. 146 - 148 (2015)
Construction of macrocyclic trienes by diene-ene RCM of tetraenes was examined. In the reactions, macrocyclic trienes were obtained as a mixture of two isomers with E,Z-configured 1,3-diene moiety. The formation of two isomers can be understandable by the
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.
Synthesis of C37-Alkenones for Past Climate Reconstructions
Berton, Giacomo,Pizzini, Sarah,Fabris, Fabrizio,Bertolin, Tommaso,Pafumi, Eugenia,Ceccon, Leonardo,Daelemans, Jonas,Borsato, Giuseppe,Scarso, Alessandro,Piazza, Rossano,Ferretti, Patrizia
, p. 3542 - 3551 (2020/03/26)
The total syntheses of three C37 methyl-alkenones with different degrees of unsaturation and of their 13C-labelled analogues from commercially available starting materials are presented herein for the first time. These molecules are important to improve the reliability of the measurements and reconstructions of the sea surface temperature and salinity.
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.
Catalyst-Controlled Diastereoselective Synthesis of Cyclic Amines via C-H Functionalization
Munnuri, Sailu,Adebesin, Adeniyi Michael,Paudyal, Mahesh P.,Yousufuddin, Muhammed,Dalipe, Alfonso,Falck, John R.
supporting information, p. 18288 - 18294 (2017/12/27)
Reliable regio- and stereochemical techniques applicable to nonactivated aliphatic systems remain largely elusive due to the challenges of discriminating between multiple, relatively strong sp3 C-H bonds whose chemical behavior often differ onl
Hexanes/acetonitrile: A binary solvent system for the efficient monosilylation of symmetric primary and secondary diols
Wilke, Burkhardt I.,Dornan, Mark H.,Yeung, Jon,Boddy, Christopher N.,Pinto, Atahualpa
, p. 2600 - 2602 (2014/05/06)
Symmetric diols are useful compounds in the synthesis of natural products, their value often dependent on their successful monoprotection. A general and simple method for the monosilylation of symmetrical primary and secondary diols is reported. The metho
Asymmetric synthesis of 3,3,5,5-tetrasubstituted 1,2-dioxolanes: Total synthesis of epiplakinic acid F
Tian, Xiang-Yin,Han, Jian-Wei,Zhao, Qiong,Wong, Henry N. C.
, p. 3686 - 3700 (2014/06/09)
The first enantioselective total synthesis of epiplakinic acid F (1) was achieved through a pivotal step involving a radical-mediated asymmetric peroxidation of vinylcyclopropanes with molecular oxygen to construct highly substituted 1,2-dioxolanes. Subsequent conversions of the chiral 1,2-dioxolanes led to total synthesis of epiplakinic acid F (1) and the confirmation of its absolute configuration. The enantiomer of epiplakinic acid F methyl ester (2) was also prepared. This journal is the Partner Organisations 2014.
