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Literature DB >> 12375965

Total synthesis of anhydrolycorinone utilizing sequential intramolecular Diels-Alder reactions of a 1,3,4-oxadiazole.

Abstract

A convergent total synthesis of anhydrolycorinone is detailed, enlisting sequential intramolecular Diels-Alder reactions of a suitably substituted 2-amino-1,3,4-oxadiazole defining a novel oxadiazole --> furan --> benzene Diels-Alder strategy.

Entities: Chemical

Mesh：

Substances：

Year: 2002 PMID： 12375965 DOI： 10.1021/jo020437k

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

23 in total

1. Intramolecular diels-alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles.

Authors: Gregory I Elliott; James R Fuchs; Brian S J Blagg; Hayato Ishikawa; Houchao Tao; Z-Q Yuan; Dale L Boger
Journal: J Am Chem Soc Date: 2006-08-16 Impact factor: 15.419

2. Triflic acid-mediated rearrangements of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: synthesis of methoxytropolones and furans.

Authors: Yvonne D Williams; Christine Meck; Noushad Mohd; Ryan P Murelli
Journal: J Org Chem Date: 2013-11-14 Impact factor: 4.354

3. Cycloadditions of 1,2,3-Triazines Bearing C5-Electron Donating Substituents: Robust Pyrimidine Synthesis.

Authors: Christopher M Glinkerman; Dale L Boger
Journal: Org Lett Date: 2015-07-14 Impact factor: 6.005

4. Inverse electron demand Diels-Alder reactions of 1,2,3-triazines: pronounced substituent effects on reactivity and cycloaddition scope.

Authors: Erin D Anderson; Dale L Boger
Journal: J Am Chem Soc Date: 2011-07-19 Impact factor: 15.419

10. Total synthesis and evaluation of vinblastine analogues containing systematic deep-seated modifications in the vindoline subunit ring system: core redesign.

Authors: Kristin D Schleicher; Yoshikazu Sasaki; Annie Tam; Daisuke Kato; Katharine K Duncan; Dale L Boger
Journal: J Med Chem Date: 2013-01-04 Impact factor: 7.446

Total synthesis of anhydrolycorinone utilizing sequential intramolecular Diels-Alder reactions of a 1,3,4-oxadiazole.

1. Intramolecular diels-alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles.

2. Triflic acid-mediated rearrangements of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: synthesis of methoxytropolones and furans.

3. Cycloadditions of 1,2,3-Triazines Bearing C5-Electron Donating Substituents: Robust Pyrimidine Synthesis.

4. Inverse electron demand Diels-Alder reactions of 1,2,3-triazines: pronounced substituent effects on reactivity and cycloaddition scope.

5. Scope of the inverse electron demand Diels-Alder reactions of 1,2,3-triazine.

6. Total synthesis of lycogarubin C and lycogalic acid.

7. Total synthesis of (+)-fendleridine (aspidoalbidine) and (+)-1-acetylaspidoalbidine.

8. Total synthesis of (-)-kopsinine and ent-(+)-kopsinine.

9. Direct Synthesis of β-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines.

10. Total synthesis and evaluation of vinblastine analogues containing systematic deep-seated modifications in the vindoline subunit ring system: core redesign.