Total synthesis of (+)-kalkitoxin.
نویسندگان
چکیده
The neurotoxic lipopeptide (+)-kalkitoxin was synthesized by a route which employed asymmetric organocopper conjugate addition followed by in situ enolate alkylation to install the anti,anti-1,2,4-trimethyl relationship of the toxin; the synthesis of kalkitoxin required sixteen steps and proceeded in 3% overall yield.
منابع مشابه
Toward ideality: the synthesis of (+)-kalkitoxin and (+)-hydroxyphthioceranic acid by assembly-line synthesis.
The iterative homologation of boronic esters using chiral lithiated benzoate esters and chloromethyllithium has been applied to the highly efficient syntheses of two natural products, (+)-kalkitoxin and (+)-hydroxyphthioceranic acid. The chiral lithiated benzoate esters (>99% ee) were generated from the corresponding stannanes, which themselves were prepared by Hoppe-Beak deprotonation of ethyl...
متن کاملKalkitoxin Inhibits Angiogenesis, Disrupts Cellular Hypoxic Signaling, and Blocks Mitochondrial Electron Transport in Tumor Cells
The biologically active lipopeptide kalkitoxin was previously isolated from the marine cyanobacterium Moorea producens (Lyngbya majuscula). Kalkitoxin exhibited N-methyl-D-aspartate (NMDA)-mediated neurotoxicity and acted as an inhibitory ligand for voltage-sensitive sodium channels in cultured rat cerebellar granule neurons. Subsequent studies revealed that kalkitoxin generated a delayed form ...
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:
- Chemical communications
دوره 16 شماره
صفحات -
تاریخ انتشار 2003