27437-03-2Relevant academic research and scientific papers
Total synthesis of (±)-naphthacemycin A 9, possessing both antibacterial activity against methicillin-resistant Staphylococcus aureus and circumventing effect of β-lactam resistance
Hirose, Tomoyasu,Kojima, Yasuhiro,Matsui, Hidehito,Hanaki, Hideaki,Iwatsuki, Masato,Shiomi, Kazuro,Omura, Satoshi,Sunazuka, Toshiaki
, p. 574 - 581 (2017)
The total synthesis of KB-3346-5A9, named naphthacemycin A9, has been accomplished by combining the D?tz reaction and Suzuki-Miyaura cross coupling as well as employing Friedel-Crafts reaction with dienone-phenol rearrangement as key steps. We also describe the preparation of the simplified tetarimycin A and naphthacemycin A analogs as a model study, which coincidentally reveal unique properties of naturally occurring naphthacene-5,6,11(12H)-trione framework. The synthesized compounds were evaluated for antibacterial activity against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus (VRE) to elucidate their structure-activity relationships (SARs), the results of which agreed with a previously reported preliminary SAR study of tetarimycin A.
Physical organic chemistry of transition metal carbene complexes. 19. Kinetics of reversible alkoxide ion addition to substituted (methoxyphenylcarbene)pentacarbonylchromium(0) and (methoxyphenylcarbene)pentacarbonyltungsten(0) in methanol and aqueous ace
Bernasconi, Claude F.,Garcia-Rio, Luis
, p. 3821 - 3829 (2007/10/03)
Rate and equilibrium constants for the nucleophilic addition of MeO- in methanol and in 90% MeCN-10% MeOH, of HC≡CCH2O- and CF3CH2O- in 50% MeCN-50% water, and of OH- in 50% MeCN
Coupling of Cyclobutenediones with Fischer Carbene Complexes: A One-Step Synthesis of Cyclopentenediones and/or 5-Alkylidenefuranones via Net Insertion of the Carbene Unit into a C - C Bond
Zora, Metin,Li, Yuhui,Herndon, James W.
, p. 4429 - 4436 (2008/10/08)
The reaction of Fischer carbene - chromium complexes with 3-cyclobutene-1,2-diones has been investigated. In most cases, the major product of the reaction is the C - C bond insertion product, a 2-alkoxy-4-cyclopentene-1,3-dione, accompanied by a minor amount of the partial deoxygenation product, a 4-cyclopentene-1,3-dione. In some cases, 5-alkylidenefuranones are also formed. A mechanism involving oxidative addition of the coordinatively unsaturated Fischer carbene complex followed by acyl migration and reductive elimination was proposed to account for cyclopentenedione formation. Furanone formation was thought to arise via demetalation of the acyl migration product, followed by O-acylation. An electronic dependence was noted for cyclopentenedione/alkylidene - furanone ratio, which was evaluated using the Hammett equation.
