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Literature DB >> 17479167

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

Abstract

A stereocontrolled and scalable synthesis of an advanced intermediate of the dysiherbaine tetrahydropyran core has been achieved in 11 steps and 27% overall yield. The key feature of this synthetic approach is the application of the Donohoe tethered aminohydroxylation reaction to install the amino diol and establish the four contiguous syn stereocenters on the tetrahydropyran ring.

Entities: Chemical Gene

Year: 2007 PMID： 17479167 PMCID： PMC1865120 DOI： 10.1016/j.tetlet.2007.02.016

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. An efficient, general asymmetric synthesis of carbocyclic nucleosides: application of an asymmetric aldol/ring-closing metathesis strategy.

Authors: M T Crimmins; B W King; W J Zuercher; A L Choy
Journal: J Org Chem Date: 2000-12-15 Impact factor: 4.354

Review 2. 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

2 in total

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

1. Total synthesis of dysiherbaine.

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

3. Efficient acyclic stereocontrol using the tethered aminohydroxylation reaction.

4. The regioselective aminohydroxylation of allylic carbamates.

5. An efficient, general asymmetric synthesis of carbocyclic nucleosides: application of an asymmetric aldol/ring-closing metathesis strategy.

6. Synthesis of (-)-dysiherbaine.

7. Divergent pharmacological activity of novel marine-derived excitatory amino acids on glutamate receptors.

8. A convenient route to the furopyran core of dysiherbaine.

Review 9. Imido-osmium(VIII) compounds in organic synthesis: aminohydroxylation and diamination reactions.

10. Effects of a new excitotoxic amino acid, dysiherbaine, on cultured Müller cells.

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

Review 2. Application of asymmetric Sharpless aminohydroxylation in total synthesis of natural products and some synthetic complex bio-active molecules.