Synthesis 2014; 46(24): 3283-3308
DOI: 10.1055/s-0033-1338650
review
© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 06 March 2014

Accepted after revision: 07 March 2014

Publication Date:
17 November 2014 (online)


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

 
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