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Literature DB >> 17691796

A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics.

Abstract

A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics is reported. The route proceeds in nine steps (21% yield) from the commercial substance methyl 3-hydroxy-5-isoxazolecarboxylate. Key steps in the route involve enantioselective addition of divinylzinc to 3-benzyloxy-5-isoxazolecarboxaldehyde and an endo-selective intramolecular furan Diels-Alder cycloaddition reaction. The route described has provided more than 40 g of chromatographically pure 1 with 93% ee.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17691796 PMCID： PMC3178443 DOI： 10.1021/ol071377d

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

3 in total

1. New Applications of Polyfunctional Organometallic Compounds in Organic Synthesis Frequently used abbreviations are defined at the end of the article.

Authors: Andreas Boudier; Lars O. Bromm; Matthias Lotz; Paul Knochel
Journal: Angew Chem Int Ed Engl Date: 2000-12-15 Impact factor: 15.336

2. A convergent enantioselective route to structurally diverse 6-deoxytetracycline antibiotics.

Authors: Mark G Charest; Christian D Lerner; Jason D Brubaker; Dionicio R Siegel; Andrew G Myers
Journal: Science Date: 2005-04-15 Impact factor: 47.728

3. The origin of the halogen effect on reactivity and reversibility of Diels-Alder cycloadditions involving furan.

Authors: Susan N Pieniazek; Kendall N Houk
Journal: Angew Chem Int Ed Engl Date: 2006-02-20 Impact factor: 15.336

3 in total

19 in total

A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics.

1. New Applications of Polyfunctional Organometallic Compounds in Organic Synthesis Frequently used abbreviations are defined at the end of the article.

2. A convergent enantioselective route to structurally diverse 6-deoxytetracycline antibiotics.

3. The origin of the halogen effect on reactivity and reversibility of Diels-Alder cycloadditions involving furan.

1. A chiral Lewis acid strategy for enantioselective allylic C-H oxidation.

Review 2. Recent advances in the chemistry and biology of naturally occurring antibiotics.

3. A practical, convergent route to the key precursor to the tetracycline antibiotics.

Review 4. Natural Products as Platforms To Overcome Antibiotic Resistance.

5. Concise Synthesis of (+)-[¹³ C₄ ]-Anatoxin-a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion.

6. A robust platform for the synthesis of new tetracycline antibiotics.

Review 7. The evolving role of chemical synthesis in antibacterial drug discovery.

8. Total synthesis and structural revision of viridicatumtoxin B.

9. The catalytic asymmetric addition of alkyl- and aryl-zinc reagents to an isoxazole aldehyde.

10. A C-H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs.