64841-44-7Relevant articles and documents
The first total synthesis of (±)-4-methoxydecanoic acid: a novel antifungal fatty acid
Carballeira, Néstor M.,Miranda, Carlos,Parang, Keykavous
, p. 5699 - 5700 (2009)
The hitherto unknown (±)-4-methoxydecanoic acid was synthesized in six steps and in 25% overall yield starting from commercially available 4-penten-1-ol. The title compound demonstrated 17-fold higher antifungal activity (MIC = 1.5 mM) against Candida albicans ATCC 60193 and Cryptococcus neoformans ATCC 66031 when compared to unsubstituted n-decanoic acid. Our results demonstrate that mid-chain methoxylation appears to be a viable strategy for increasing the fungitoxicity of fatty acids.
On-Line Polyketide Cyclization into Diverse Medium-Sized Lactones by a Specialized Ketosynthase Domain
Sundaram, Srividhya,Kim, Hak Joong,Bauer, Ruth,Thongkongkaew, Tawatchai,Heine, Daniel,Hertweck, Christian
, p. 11223 - 11227 (2018)
Ketosynthase (KS) domains of modular type I polyketide synthases (PKSs) typically catalyze the Claisen condensation of acyl and malonyl units to form linear chains. In stark contrast, the KS of the rhizoxin PKS branching module mediates a Michael addition, which sets the basis for a pharmacophoric δ-lactone moiety. The precise role of the KS was evaluated by site-directed mutagenesis, chemical probes, and biotransformations. Biochemical and kinetic analyses helped to dissect branching and lactonization reactions and unequivocally assign the entire sequence to the KS. Probing the range of accepted substrates with diverse synthetic surrogates in vitro, we found that the KS tolerates defined acyl chain lengths to produce five- to seven-membered lactones. These results show that the KS is multifunctional, as it catalyzes β-branching and lactonization. Information on the increased product portfolio of the unusual, TE-independent on-line cyclization is relevant for synthetic biology approaches.
Light-promoted metal-free cross dehydrogenative couplings on ethers mediated by NFSI: Reactivity and mechanistic studies
Beniazza, Redouane,Abadie, Baptiste,Remisse, Lionel,Jardel, Damien,Lastécouères, Dominique,Vincent, Jean-Marc
supporting information, p. 12708 - 12711 (2017/12/02)
Cross dehydrogenative couplings on ethers occur very effectively using N-fluorobis(phenyl)sulfonimide (NFSI) as oxidizing agent under UVA irradiation in the presence of 2 mol% benzophenone. The reaction was shown to proceed first by fast radical fluorination of the α-C-H bond of ethers, followed by HF elimination to yield the highly electrophilic oxocarbenium ion as a key intermediate.
Unexpected Mild Protection of Alcohols as 2-O-THF and 2-O-THP Ethers Catalysed by Cp2TiCl Reveal an Intriguing Role of the Solvent in the Single-Electron Transfer Reaction
Durán-Pe?a, María Jesús,Botubol-Ares, José Manuel,Hanson, James R.,Hernández-Galán, Rosario,Collado, Isidro G.
, p. 6333 - 6340 (2015/10/06)
A method for the conversion of primary, secondary and tertiary alcohols into the corresponding THF ethers at room temperature and primary and secondary alcohols into the corresponding THP ethers, has been developed using titanium(III) species generated from a catalytic amount of titanocene dichloride or (4R,5R)-(-)-2,2-dimethyl-α,α,α′,α′-tetra(1-naphthyl)-1,3-dioxolane-4,5-dimethanolatotitanium(IV) dichloride:acetonitrile adduct together with manganese(0) as a reductant and bromoform in THF or THP as the solvent. A radical mechanism is proposed for this transformation revealing an intriguing role of the solvent in the single-electron transfer reactions catalysed by the low valent TiIII system. A set of primary, secondary and benzylic alcohols have been converted into the corresponding THF and THP ethers and tertiary alcohols into the corresponding THF ethers using a catalytic amount of titanium dichloride in good yields and mild reaction conditions.
Stereoselective Synthesis of (10 S,12 S)-10-Hydroxy-12-methyl-1-oxacyclododecane-2,5-dione via Prins Cyclization
Yadav,Thrimurtulu,Venkatesh,Rao, K. V. Raghavendra,Prasad,Reddy, B. V. Subba
experimental part, p. 73 - 78 (2010/04/26)
The total synthesis of (10S,12S)-10-hydroxy-12-methyl-1-oxacyclododecane-2,5-dione is described proving the versatility of the Prins cyclization in natural products synthesis. The approach is convergent and highly stereoselective. Prins cyclization, ester
Synthesis of novel 5-substituted pyrazole derivatives as cannabinoid antagonists
Alekseeva, Olga O.,Mahadevan, Anu,Wiley, Jenny L.,Martin, Billy R.,Razdan, Raj K.
, p. 2159 - 2161 (2007/10/03)
A facile seven-step sequence was developed from 4′- bromopropiophenone, utilizing a Suzuki-type coupling with an alkene, to give several novel 5-substituted pyrazole derivatives in overall yields of 11-31%. They are potent CB1 antagonists and have binding
Palladium(II)-catalyzed oxidation of terminal alkenes to methyl ketones using molecular oxygen
Nishimura, Takahiro,Kakiuchi, Nobuyuki,Onoue, Tomoaki,Ohe, Kouichi,Ucmura, Sakae
, p. 1915 - 1918 (2007/10/03)
Palladium(II) acetate catalyzes the aerobic oxidation of terminal alkenes in toluene into the corresponding methyl ketones in the presence of a catalytic amount of pyridine using propan-2-ol as a reductant and molecular oxygen as an oxidant. Two catalytic cycles sharing a Pd(II)-OOH species are proposed. One is the formation of a Pd(II)-H species in the oxidation of propan-2-ol to acetone, followed by reaction with molecular oxygen to give a Pd(II)-OOH species, and the other is peroxypalladation of an alkene with the Pd(II)-OOH species produced to afford a methyl ketone in the presence of H2O2 produced by the former catalytic cycle. The Royal Society of Chemistry 2000.
Synthesis of (Z)-6-heneicosen-11-one, (+/-)(Z)-14-methyl-8-hexadecen-1-ol and (+/-)-5,6-dehydrosenedigitalene
Sharma, M. L.,Verma, Sadhana,Chand, Tek
, p. 1030 - 1034 (2007/10/03)
Three naturally occurring compounds (Z)-6-heneicosen-11-one (1), (+/-)-(Z)-14-methyl-8-hexadecen-1-ol (2) and (+/-)-5,6-dehydrosenedigitalene (3) have been synthesised using lithium tetrachlorocuperate catalysed coupling reaction.
Ceric ammonium nitrate catalysed protection of alcohols by 3,4-dihydro-2H-pyran
Maity,Roy
, p. 1667 - 1671 (2007/10/02)
Hydroxyl compounds readily add to dihydropyran in presence of a catalytic amount of ceric ammonium nitrate to give high yield of tetrahydropyranyl ethers.
Intramolecularly Alkylated Salen Complexes: New Models for Coenzyme B12 with a Cobalt-to-Ligans Carbon Bridge
Arkel, Bert van,Baan, Juul van der,Balt, Sijbe,Bickelhaupt, Friedrich,Bolster, Martinus W. G. de,et al.
, p. 3023 - 3032 (2007/10/02)
The synthesis of H2salen diphenol> derived models 1 for coenzyme B12 with a carbon bridge between the ligand and cobalt has been accomplished by condensation of salicylaldehyde and ω-substituted 1,2-diamines 8
