Synthesis of highly enantio-enriched stereoisomers of hydroxy-GR24.

نویسندگان

  • J C Morris
  • C S P McErlean
چکیده

In contrast to a biomimetic electrophilic cyclisation cascade, we employ a contra-biomimetic nucleophilic cyclisation cascade to give the tricyclic core of 4-hydroxy-GR24 in a single step. Kinetic resolution using a stereoselective Noyori transfer hydrogenation enables the concise synthesis of any enantiomerically enriched 4-hydroxy-GR24 stereoisomer.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Concise Asymmetric Synthesis and Pharmacological Characterization of All Stereoisomers of Glutamate Transporter Inhibitor TFB-TBOA and Synthesis of EAAT Photoaffinity Probes.

Glutamate is the major excitatory neurotransmitter in the mammalian brain. Its rapid clearance after the release into the synaptic cleft is vital in order to avoid toxic effects and is ensured by several transmembrane transport proteins, so-called excitatory amino acid transporters (EAATs). Impairment of glutamate removal has been linked to several neurodegenerative diseases and EAATs have ther...

متن کامل

A Practical Chemo-enzymatic Approach to Highly Enantio-Enriched 10-Ethyl-7,8-dihydro-γ-ionone Isomers: A Method for the Synthesis of 4,5-Didehydro-α-Ionone

An efficient and convenient strategy for the enantioselective synthesis of enantiomerically enriched 10-ethyl-7,8-dihydro-γ-ionone isomers (R)-(+)-7, and (S)-(-)-7 are described utilizing a lipase mediated resolution protocol, and reductive elimination of the secondary allylic alcohol as the key step. The enantioselective and diastereoselective lipase kinetic acetylation of 4-hydroxy-γ-ionone d...

متن کامل

Reaction between 3-hydroxy pyridine alkyl isocyanides and dialkyl acetylenedicarboxylate: synthesis of 4H-chromenes

The reactive intermediate generated by the addition of tert-butyl and 1,1,3,3-tetramethyl butyl isocyanide and cyclohexyl isocyanide to dialkyl acetylenedicarboxylate was trapped by 3-hydroxy pyridine to produce highly functionalized 4H-chromenes in fairly good  yields.

متن کامل

Condensationtion of 3-hydroxy pyridine alkyl isocyanides and dialkyl acetylenedicarboxylate: synthesis of 4H-chromenes

The reactive intermediate generated by the addition of tert-butyl and 1,1,3,3-tetramethyl butyl isocyanide and cyclohexyl isocyanide to dialkyl acetylenedicarboxylate was trapped by 3-hydroxy pyridine to produce highly functionalized 4H-chromenes in fairly good  yields.

متن کامل

ذخیره 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 نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 14 4  شماره 

صفحات  -

تاریخ انتشار 2016