An enantioselective formal synthesis of (+)-Gephyrotoxin 287C
نویسندگان
چکیده
The tricyclic skeleton of the gephyrotoxin amphibian alkaloids was synthesized via an enantioselective serial sequence involving nine discrete steps that furnished Kishi’s intermediate 5 in 22% overall yield. This efficient and expeditious synthetic approach exploits the inherent stereochemistry of a (1R)-2-tropinone derivative for the construction of the core cis-2,5disubstituted pyrrolidine ring system and constitutes a formal synthesis of gephyrotoxin 287C.
منابع مشابه
Chemoenzymatic Enantioselective Formal Synthesis of (-)-Gephyrotoxin-223
(-)-Gephyrotoxin-223 was formally synthesized from chiral synthon 1 which has been chemoenzymatically synthesized in the presence of Candida Antartica lipase.
متن کاملAn Efficient and One-pot Procedure for the Synthesis of Chiral Isoxazolidine via Catalytic Highly Enantioselective 1,3-dipolar cycloaddition
Synthesis of enantiomerically pure isoxazolidine via an asymmetric 1,3- dipolar cycloaddition reaction of nitrone with electron-deficient dipolarophile was described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendate bis(imine)–Cu(II)triflate complex as catalyst. The reaction mechanism is discussed on the basis of the assignment of t...
متن کاملUltrasonic Irradiation Assisted Enantioselective Synthesis of Alzheimer’s Disease Drug Rivastigmine Tartrate by Using Nanocatalyst
A highly efficient and convenient procedure for the enantioselective synthesis of (S)-Rivastigmine tartrate, a cholinergic agent for the treatment of mild to moderate dementia of the Alzheimer’s disease, is accomplished by the treatment of versatile, readily accessible N-Ethyl-N-methyl carbamoyl chloride with 3-hydroxyacetophenone under ultrasonic irradiation in presence of nano-K2CO3 were repo...
متن کاملEnantioselective formal total synthesis of (-)-dysidiolide.
[reaction: see text] An enantioselective formal total synthesis of the sesterterpene (-)-dysidiolide 1 beginning with an intermolecular Diels-Alder reaction of the allene ester 3 and the silyloxydiene 10 is reported.
متن کاملA Catalytic, Enantioselective Formal Synthesis of (+)-Dichroanone and (+)-Taiwaniaquinone H
A catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone H is reported. The all-carbon quaternary stereocenter was constructed by asymmetric conjugate addition catalyzed by a palladium(II) (S)-tert-butylpyridinooxazoline complex. The unexpected formation of a [3.2.1] bicyclic intermediate required the identification of a new route. Analysis of the Hammett consta...
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:
دوره شماره
صفحات -
تاریخ انتشار 2010