Total synthesis of (-)-acutumine.
نویسندگان
چکیده
The first total synthesis of the tetracyclic alkaloid (-)-acutumine is described. Key reactions include an asymmetric ketone allylation mediated by Nakamura's chiral allylzinc reagent, an anionic oxy-Cope rearrangement, and the Lewis acid-promoted cyclization of an amine onto an alpha,beta-unsaturated dimethyl ketal.
منابع مشابه
Rapid construction of the aza-propellane core of acutumine via a photochemical [2 + 2] cycloaddition reaction.
Synthetic efforts toward the chlorinated aza-propellane alkaloid acutumine (1) are described. The key vicinal quaternary centers were constructed by a photochemical [2 + 2] cycloaddition reaction of a furanyl-tetrahydroindolone. Dihydroxylation of the [2 + 2] product enabled a tandem retro-aldol/intramolecular ketalization reaction, which revealed the aza-propellane core of 1 while generating a...
متن کاملSpiroketals via oxidative rearrangement of enol ethers.
Oxidative rearrangement of cyclic enol ethers leads to alpha-alkoxyesters. In the presence of a neighboring spiroether, this approach provides a stereoselective access to spiroketals. A modified proposal for the biosynthesis of acutumine is presented.
متن کاملGreen Synthesis of Silver Nanoparticles and Its Effect on Total Proteins in Melia Azedarach Plant
Silver nano-particles have different biological applications due to their compatibility. Chemical methods usually result in remaining some amounts of toxic reactions on the nano-particles. For this reason, the use of plants as sustainable and accessible resources in preparation of compatible nano-particles has attracted a lot of attention in the recent years. This research investigated the gree...
متن کاملOptimization of biocatalytic synthesis of Chitosan Ester using response surface methodology
Esterification of chitosan with adipic acid catalyzed by immobilized Candida antarctica lipase B was carried out in this study. Response surface methodology (RSM) based on a four-factor- five-level small central composite design (SCCD) was employed to model and analyze the reaction. A total of 21 experiments representing different combinations of the four reaction parameters including ch...
متن کاملTotal Phenolic and Flavonoids Contents, Radical Scavenging Activity and Green Synthesis of Silver Nanoparticles by Laurus nobilis L. Leaves Aqueous Extract
In this project, total phenolic and flavonoid contents of the aqueous extract of Laurus nobilis L. leaves were evaluated by colorimetric methods. These natural products which are found in plants extracts, can be considered as reducing and stabilizing agents in the synthesis of metal nanoparticles. Regarding to high amounts of these compounds in the extract, silver nanoparticles were synthesized...
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:
- Journal of the American Chemical Society
دوره 131 19 شماره
صفحات -
تاریخ انتشار 2009