Asymmetric total synthesis of martinelline and martinellic acid.
نویسندگان
چکیده
Herein, we describe the first asymmetric total synthesis of (-)-martinelline ((-)-2) and the second total synthesis of (-)-martinellic acid ((-)-1) by employing a tandem Mukaiyama-Mannich reaction/aminal cyclization as the key step.
منابع مشابه
Synthesis of hexahydrofuro[3,2-c]quinoline, a martinelline type analogue and investigation of its biological activity.
BACKGROUND Candida susceptibility commonly occurs in breast cancer patients. Of which, Candida albicans is considered as a common pathogen causing candidiasis. Martinella iquitosensis (Bignoniaceae) is one of the species belonged to Martinella, distributed widely in Amazon basin. Its root extract yielded two complex substituted tetrahydroquinolines, Martinelline and Martinellic acid which were ...
متن کاملAn expedient approach to pyrrolo[3,2-c]quinolines via regioselective formation of the pyrrole nucleus over indoles.
An efficient approach for the synthesis of pyrrolo[3,2-c]quinolines (the core nucleus of the natural product martinellic acid) from protected 2-alkynylanilines via the regioselective formation of pyrroles followed by Heck and intramolecular Michael addition has been described.
متن کاملAsymmetric Synthesis of Modafinil and its Derivatives by using the Functionalized Silica-based Mesoporous MCM-41
Modafinil [2-[(diphenylmethyl)sulfinyl]acetamide] is used clinically in the treatment of narcolepsy and sleeping disorders. The synthesis of modafinil, begins with the reaction of benzhydrol and thioglycolic acid in trifluoroacetic acid to afford benzhydrylsulfinyl acetic acid. The reaction of acid with thionyl chloride in benzene followed by treatment with ammonium hydroxide gave acetamide...
متن کاملA Crystallization-Induced Asymmetric Transformation using Racemic Phenyl Alanine Methyl Ester Derivatives as Versatile Precursors to Prepare Amino Acids
L-Tyrosine and L-Dopa are the precursors in the biological synthesis of amine neurotransmitters. On the other hand, phenylalanine as an aromatic amino acid (AAA) is a precursor in the synthesis of L-Tyrosine and L-Dopa. For some substrates such as amino acids, resolution by the formation of diastereomers offers an attractive alternative. Among different methods in this case, crystallization-ind...
متن کاملOne Pot Synthesis of Highly Functionalized Tetrahydropyridines Using Nano-TiCl2/cellulose as Biodegradable and Eco-Friendly Catalyst
TiCl4/nano-cellulose as a biodegradable and eco-friendly Lewis acid catalyst was synthesized via reaction of nano-cellulose and TiCl4. This catalyst was characterized and used for synthesis of asymmetric highly functionalized tetrahydropyridines via a five-component condensation reaction of p-substituted anilines, aldehydes and ethyl acetoacetate under solvent-free condition. Simple methodology...
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 5 شماره
صفحات -
تاریخ انتشار 2007