Furan Oxidation Reactions in the Total Synthesis of Natural Products

Anton S. Makarov; Maxim G. Uchuskin; Igor V. Trushkov

doi:10.1055/s-0037-1610021

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(16): 3059-3086
DOI: 10.1055/s-0037-1610021

review

Furan Oxidation Reactions in the Total Synthesis of Natural Products

Anton S. Makarov

^aDepartment of Chemistry, Perm State University, Bukireva 15, Perm 614990, Russian Federation eMail: mu@psu.ru

,

Maxim G. Uchuskin*

^aDepartment of Chemistry, Perm State University, Bukireva 15, Perm 614990, Russian Federation eMail: mu@psu.ru

,

Igor V. Trushkov*

^bDmitry Rogachev National Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela 1, Moscow 117997, Russian Federation eMail: itrushkov@mail.ru

^cFaculty of Science, Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya 6, Moscow 117198, Russian Federation

› Institutsangaben

Abstract

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Abstract

Recent developments on the transformations of furans under oxidative conditions toward the total synthesis of complex natural compounds are discussed. Reactions and methods are classified according to the type of oxidant used. Comparisons are then made between all the strategies to provide a comprehensive overview. This review covers the most prominent work published from 2011 until 2017.

1 Introduction

2 Reagents and Methods for Oxidation of the Furan Ring

2.1 Singlet Oxygen

2.2 Peroxides and Hydroperoxides

2.3 Quinones

2.4 Halogen-Based Oxidants

2.5 Chromium-Based Oxidants

3 The Achmatowicz Reaction

3.1 Halogen-Based Oxidants

3.2 Hydroperoxides

3.3 Enzymatic Oxidation

4 Conclusion

Key words

furans - oxidation - rearrangement - natural products - total synthesis

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