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Synthesis 2014; 46(24): 3283-3308
DOI: 10.1055/s-0033-1338650
DOI: 10.1055/s-0033-1338650
review
The Glycol Cleavage in Natural Product Synthesis: Reagent Classics and Recent Advances
Weitere Informationen
Publikationsverlauf
Received: 06. März 2014
Accepted after revision: 07. März 2014
Publikationsdatum:
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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For a review, see:
For related glycol cleavages of the tetrapyrrole core, see:
For reviews, see:
It should be noted that there were previous reports on silica gel supported periodate but such reagents appear not to be as practical as the reagent described in ref. 44a; see:
For related work, see:
For reviews, see:
For an early result on the Dess–Martin periodinane mediated cleavage of vicinal diols, see: