Synthesis of (-)-tetrodotoxin: preparation of an advanced cyclohexenone intermediate.
نویسندگان
چکیده
The preparation of an advanced intermediate toward the enantioselective synthesis of tetrodotoxin is outlined. The enantiomerically pure cyclopentene 15 was generated from ketone 14 by alkylidene carbene insertion with retention of absolute configuration. An ozonolysis/aldol sequence first produced the trans cyclohexenone, which upon epimerization gave the more stable cis enone 18.
منابع مشابه
The synthesis of Beta-Carbonhomologous Intermediate of Norcardicin A. A General Method for Selective Preparation of The Beta-Lactam Ring in the Presence of Free Phenolic Hydroxyl Groups
The synthesis of cis-N-[a-carbobenzyloxy-b-(p-hydroxyphenyl)ethyl]-3-phthalimido-4-styryl-2-azetidinone is described. We have found that the electron-rich Schiff bases can afford the cis-b-lactam ring even in the presence of the free hydroxyl functions. The mechanisms of cis and trans-b-lactam ring formation are discuss...
متن کاملIntermediate and Advanced EFL Learners’ Identity Reflection
Although scientific forum has obliged its members to hide their presence particularly while they are discussing research outcomes to avoid personal biases, a recent trend is encouraging writers to demonstrate their identity as the author of the text through the use of first person pronouns in order to take responsibility for the content. Therefore, the present study focuses on intermediate and ...
متن کاملA Tandem Scalable Microwave-Assisted Williamson Alkyl Aryl Ether Synthesis under Mild Conditions
An efficient tandem synthesis of alkyl aryl ethers, including valuable building blocks of dialdehyde and dinitro groups under microwave irradiation and solvent free conditions on potassium carbonate as a mild solid base has been developed. A series of alkyl aryl ethers were obtained from alcohols in excellent yields by following the Williamson ether synthesis protocol under practical mild condi...
متن کاملROLE OF Mn(TPP)Cl IN THE EPOXIDATION WITH SINGLET OXYGEN
Mn(TPP)Cl catalyzes cooxidation of olefin in the singlet oxygenation of sulfid. Mn(TPP)Cl is able to transfer an oxygen atom from a peroxidic intermediate generated in singlet oxygenation of sulfide to a metal ion affording metal 0x0 species which is responsible for epoxidation. This system leads to allcenes epoxidation such as styrene and cyclooctene. Epoxidation of cyclohexene produces cy...
متن کاملFrom egg shell wastes (ESWs) into advanced materials: A rapid and simple synthesis of CaO/Ca2Fe2O5 as a novel nanocomposite-derived ESW biomaterial
AbstractESW as a natural byproduct, although non-hazardous and contains calcium, magnesium carbonate and protein, is commonly disposed in landfills without any pretreatment because it was traditionally useless. In this regards, we wish to report the synthesis of a novel CaO/Ca2Fe2O5 nanocomposite based on ESW. At the first, eggshell (ES) nanopowder was prepared by ball-milling. Then, the ...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- The Journal of organic chemistry
دوره 68 20 شماره
صفحات -
تاریخ انتشار 2003