Literature DB >> 21822338

Synthesis of the dysiherbaine tetrahydropyran core utilizing improved tethered aminohydroxylation conditions.

Christopher L Carroll1, A Richard Chamberlin.   

Abstract

A concise stereoselective route to the dysiherbaine tetrahydropyran core was achieved in 9 steps and 39% overall yield. Donohoe's improved tethered aminohydroxylation conditions were employed to concurrently install the amino and alcohol groups and construct the tetrahydropyran ring, which features four contiguous cis-stereocenters.

Entities:  

Year:  2011        PMID： 21822338      PMCID： PMC3148768          DOI： 10.1016/j.tetlet.2011.05.106

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  14 in total

1.  Total synthesis of dysiherbaine.

Authors:  Dean Phillips; A Richard Chamberlin
Journal:  J Org Chem       Date:  2002-05-17       Impact factor: 4.354

2.  Differential activation of individual subunits in heteromeric kainate receptors.

Authors:  Geoffrey T Swanson; Tim Green; Ryuichi Sakai; Anis Contractor; Wesley Che; Hisao Kamiya; Stephen F Heinemann
Journal:  Neuron       Date:  2002-05-16       Impact factor: 17.173

3.  Efficient acyclic stereocontrol using the tethered aminohydroxylation reaction.

Authors:  Timothy J Donohoe; Peter D Johnson; Richard J Pye; Martine Keenan
Journal:  Org Lett       Date:  2004-07-22       Impact factor: 6.005

4.  The regioselective aminohydroxylation of allylic carbamates.

Authors:  T J Donohoe; P D Johnson; M Helliwell; M Keenan
Journal:  Chem Commun (Camb)       Date:  2001-10-21       Impact factor: 6.222

5.  The tethered aminohydroxylation (TA) reaction.

Authors:  Timothy J Donohoe; Peter D Johnson; Richard J Pye
Journal:  Org Biomol Chem       Date:  2003-06-21       Impact factor: 3.876

6.  Synthesis of (-)-dysiherbaine.

Authors:  B B Snider; N A Hawryluk
Journal:  Org Lett       Date:  2000-03-09       Impact factor: 6.005

Review 7.  Excitatory amino acid agonists and antagonists: pharmacology and therapeutic applications.

Authors:  D G Trist
Journal:  Pharm Acta Helv       Date:  2000-03

Review 8.  Molecular biology of glutamate receptors in the central nervous system and their role in excitotoxicity, oxidative stress and aging.

Authors:  E K Michaelis
Journal:  Prog Neurobiol       Date:  1998-03       Impact factor: 11.685

9.  Synthesis of the dysiherbaine tetrahydropyran core employing a tethered aminohydroxylation reaction.

Authors:  Jamie L Cohen; A Richard Chamberlin
Journal:  Tetrahedron Lett       Date:  2007-04-02       Impact factor: 2.415

10.  N-sulfonyloxy carbamates as reoxidants for the tethered aminohydroxylation reaction.

Authors:  Timothy J Donohoe; Majid J Chughtai; David J Klauber; David Griffin; Andrew D Campbell
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419
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  1 in total

Review 1.  Application of asymmetric Sharpless aminohydroxylation in total synthesis of natural products and some synthetic complex bio-active molecules.

Authors:  Majid M Heravi; Tahmineh Baie Lashaki; Bahareh Fattahi; Vahideh Zadsirjan
Journal:  RSC Adv       Date:  2018-02-09       Impact factor: 4.036
  1 in total

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