The Glycol Cleavage in Natural Product Synthesis: Reagent Classics and Recent Advances

Andrea-Katharina C. Schmidt; Christian B. W. Stark

doi:10.1055/s-0033-1338650

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(24): 3283-3308
DOI: 10.1055/s-0033-1338650

review

The Glycol Cleavage in Natural Product Synthesis: Reagent Classics and Recent Advances

Andrea-Katharina C. Schmidt

Universität Hamburg, Fachbereich Chemie, Institut für Organische Chemie, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany Fax: +49(40)428384325 eMail: stark@chemie.uni-hamburg.de

,

Christian B. W. Stark*

Universität Hamburg, Fachbereich Chemie, Institut für Organische Chemie, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany Fax: +49(40)428384325 eMail: stark@chemie.uni-hamburg.de

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

This review focuses on the application of glycol cleavage reactions in the synthesis and derivatization of complex natural products. Reagent classics as well as recent developments are discussed.

1 Introduction

2 Mechanistic Aspects

3 Reagents and Examples

3.1 Periodate and Hypervalent Iodine

3.1.1 Periodic Acid and Periodates

3.1.2 Periodate on Wet Silica Gel

3.1.3 Phenyliodine Diacetate

3.1.4 Other Iodine Reagents

3.2 Lead Tetraacetate

3.3 Chromium Reagents

3.3.1 Pyridinium Chlorochromate

3.3.2 Other Chromium Reagents

3.4 Ruthenium Reagents

3.4.1 Tetra-n-propylammonium Perruthenate

3.4.2 Other Ruthenium Reagents

3.5 Manganese Reagents

3.5.1 Manganese(III) Acetate

3.5.2 Manganese Dioxide

3.5.3 Other Manganese Reagents

3.6 Miscellaneous

4 Conclusion

Key words

oxidation - diols - glycol cleavage - natural products - total synthesis

Volltext

Referenzen

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