Synthesis of bridged oxafenestranes from pleuromutilin.
نویسندگان
چکیده
Fenestranes are an intriguing class of highly strained molecules possessing a quaternary carbon with bonds that deviate from the canonical tetrahedral geometry. Herein we report the discovery that the natural product pleuromutilin can be used as a structurally complex starting material for the synthesis of a series of bridged cis,cis,cis,cis-[4.5.5.5]- and cis,cis,cis,cis-[4.5.7.5]oxafenestranes through a carbocation rearrangement cascade. X-ray crystallographic analysis of several cis,cis,cis,cis-[4.5.5.5]oxafenestranes shows a significant planarization of the central tetracoordinate carbon atom and demonstrates the influence of bridgehead substituents and bridging rings on planarity.
منابع مشابه
Synthesis of Bridged Bithiazoles
Bridged bithiazoles (5,5'-ethylene-4,4'-bithiazoles) are synthesized as a good chelating agent.
متن کاملExpanding the pleuromutilin class of antibiotics by de novo chemical synthesis.
New pleuromutilin-like compounds were synthesized in approximately 11 steps from 3-allylcyclopent-2-enone by a strategy featuring sequential carbonyl addition reactions. Several analogs possessing the C14 tiamulin ester side chain displayed activity in a Mycobacterium tuberculosis mc(2)7000 assay. The results described herein provide a basis for further efforts to expand the structural and ster...
متن کاملSynthesis, Characterization and Antibacterial Properties of Some Thiocyanato Bridged Heteronuclear Complexes of Nickel
A series of heterobinuclear, thiocyanato-bridged complexes of cations [M(NH2X)6 ] 2+, and [M(en)3 ] 2+ (where X = H, Ph; M=Cu, Co, Cd, Zn) with anion [Ni(NCS)4 ] 2 –have been prepared by 1:1 molar ratio. The complexes have been characterized by FT-IR, 13C NMR and UV-vis spectroscopy, metal analysis, magnetic and conductance studies. The complexes have the following composition: [M(NH2 X)5 ][Ni(...
متن کاملA concise synthesis of the molecular framework of pleuromutilin.
Two syntheses of the tricyclic carbon skeleton of pleuromutilin are reported. Diastereoselective 1,4-conjugate additions were used to elaborate bicyclic precursors at an early stage of each route, while ring-forming olefin metatheses were executed to complete the pleuromutilin carbon framework. The congeners prepared are appropriately functionalized to enable access to diverse pleuromutilin ana...
متن کاملSynthesis and in Vitro Antibacterial Activity of Four Novel Pleuromutilin Derivatives
Four novel pleuromutilin derivatives with butyl amine group in the C-14 side-chain were designed, synthesized and confirmed by FT-IR, 1H-NMR and HRMS. The results of antibacterial activity showed that the antibacterial activity of pleuromutilin derivatives could be affected by the steric hindrance of their C-14 side-chain.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Angewandte Chemie
دوره 53 37 شماره
صفحات -
تاریخ انتشار 2014