34386-60-2Relevant academic research and scientific papers
Total Synthesis of Laspartomycin C and Characterization of Its Antibacterial Mechanism of Action
Kleijn, Laurens H. J.,Oppedijk, Sabine F.,T Hart, Peter,Van Harten, Roel M.,Martin-Visscher, Leah A.,Kemmink, Johan,Breukink, Eefjan,Martin, Nathaniel I.
, p. 3569 - 3574 (2016)
Laspartomycin C is a lipopeptide antibiotic with activity against a range of Gram-positive bacteria including drug-resistant pathogens. We report the first total synthesis of laspartomycin C as well as a series of structural variants. Laspartomycin C was found to specifically bind undecaprenyl phosphate (C55-P) and inhibit formation of the bacterial cell wall precursor lipid II. While several clinically used antibiotics target the lipid II pathway, there are no approved drugs that act on its C55-P precursor.
A practical synthesis of long-chain iso-fatty acids (iso-C 12-C19) and related natural products
Richardson, Mark B.,Williams, Spencer J.
supporting information, p. 1807 - 1812 (2013/10/22)
A gram-scale synthesis of terminally-branched iso-fatty acids (iso-C 12-C19) was developed commencing with methyl undec-10-enoate (methyl undecylenate) (for iso-C12-C14) or the C15 and C16 lactones pentadecanolide (for iso-C 15-C17) and hexadecanolide (for iso-C18-C 19). Central to the approaches outlined is the two-step construction of the terminal isopropyl group through addition of methylmagnesium bromide to the ester/lactones and selective reduction of the resulting tertiary alcohols. Thus, the C12, C17 and C18 iso-fatty acids were obtained in three steps from commercially-available starting materials, and the remaining C13-C16 and C19 iso-fatty acids were prepared by homologation or recursive dehomologations of these fatty acids or through intercepting appropriate intermediates. Highlighting the synthetic potential of the iso-fatty acids and various intermediates prepared herein, we describe the synthesis of the natural products (S)-2,15-dimethylpalmitic acid, (S)-2-hydroxy-15-methylpalmitic acid, and 2-oxo-14-methylpentadecane.
A mild and versatile method for the synthesis of alkyl ethers from methoxymethyl ethers and application to the preparation of sterically crowded ethers
Minamitsuji, Yutaka,Kawaguchi, Atsuhisa,Kubo, Ozora,Ueyama, Yoshifumi,Maegawa, Tomohiro,Fujioka, Hiromichi
supporting information; experimental part, p. 1861 - 1866 (2012/09/22)
A mild and divergent route for the synthesis of alkyl ethers from methoxymethyl (MOM) and methoxyethyl (ME) ether derivatives via pyridinium-type salt intermediates has been developed. The addition of organocuprates to the salts afforded the corresponding alkyl ethers, including highly crowded ones, in high yields even in the presence of acid- or base-sensitive functional groups. Copyright
A new synthetic method for methyl ketones from carboxylic acids using metallic strontium and methyl iodide
Miyoshi, Norikazu,Matsuo, Tsuyoshi,Asaoka, Masashi,Matsui, Aki,Wada, Makoto
, p. 28 - 29 (2007/10/03)
Carboxylic acids reacted with metallic strontium and methyl iodide to give methyl ketones preferentially in moderate to good yields. Copyright
The chemistry of alkylstrontium halide analogues, Part 2: Barbier-type dialkylation of esters with alkyl halides
Miyoshi, Norikazu,Matsuo, Tsuyoshi,Wada, Makoto
, p. 4253 - 4255 (2007/10/03)
The chemistry of an alkylstrontium halide analogue was examined. In the presence of metallic strontium, the Barbier-type alkylation of esters with alkyl iodides proceeded smoothly at room temperature, under argon, to afford the corresponding dialkylated alcohols in good yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
CuCl2.2H2O MeOH. A new reagent system for the deprotection of tetrahydropyranyl ethers
Davis, K. Joju,Bhalerao,Vittal Rao
, p. 2301 - 2308 (2007/10/03)
Cupric chloride dihydrate in methanol cleave the tetrahydropyranyl ethers to the corresponding alcohols in excellent yields under mild conditions.
