<i>anti</i>-Oligoannelated THF Moieties: Synthesis via <i>Push−Pull</i>-Substituted Cyclopropanes

Schneider, Tobias; Kaschel, Johannes; Dittrich, Birger; Werz, Daniel B.

doi:10.1021/ol900694m

Cited by 99 publications

(25 citation statements)

References 59 publications

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“…[ 2-Iodoxybenzoic Acid (IBX) ously undergo rearrangement under ring expansion to give the five-membered ring (Scheme 20). [138] A modification of this reaction yields spiroketals. [139]…”

Section: Oxidative One-pot Proceduresmentioning

confidence: 99%

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2‐Iodoxybenzoic Acid—A Simple Oxidant with a Dazzling Array of Potential Applications

2011

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Since its discovery by Christoph Hartmann and Victor Meyer in 1893, 2-iodoxybenzoic acid (IBX) has emerged as a rather ubiquitous oxidant for organic synthesis. The past decade has seen the development of a large variety of applications that go far beyond the simple oxidation of alcohols. This Review is concerned with the synthetic potential of IBX, with particular emphasis on uncommon reactivity patterns and novel fields of application.

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“…[ 2-Iodoxybenzoic Acid (IBX) ously undergo rearrangement under ring expansion to give the five-membered ring (Scheme 20). [138] A modification of this reaction yields spiroketals. [139]…”

Section: Oxidative One-pot Proceduresmentioning

confidence: 99%

“…Oxidative synthesis of anti-fused oligoacetals. [138] Scheme 21. Oxidation with IBX in the total synthesis of the macrolide (À)-amphidinolide E. [140] MOM = CH 2 OCH 3 ; TIPS = SiiPr 3 .…”

Section: Selected Applications In Total Synthesismentioning

confidence: 99%

2‐Iodoxybenzoic Acid—A Simple Oxidant with a Dazzling Array of Potential Applications

2011

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“…Bei der Oxidation von Cyclopropylmethanolderivaten wie 60 entstehen wahrscheinlich intermediär die nicht isolierbaren Cyclopropylaldehyde, die als zugleich donor-und akzeptorsubstituierte Cyclopropane ("Push-Pull-substituierte Cyclopropane") instabil sind und spontan unter Ringerweiterung zum Fünfring umlagern (Schema 20). [138] Bei einer Variante dieser Reaktion bilden sich Spiroketale. [139] 3.2.…”

Section: Methodsunclassified

“…Oxidative Synthese anti-verknüpfter Oligoacetale. [138] Schema 21. Oxidation mit IBX in der Totalsynthese des Makrolids (À)-Amphidinolid E. [140] MOM = CH 2 OCH 3 ; TIPS = SiiPr 3 .…”

Section: Alternative Protokolleunclassified

2‐Iodoxybenzoesäure – ein einfaches Oxidationsmittel mit einer Vielfalt an Anwendungsmöglichkeiten

Duschek

Kirsch

2011

Angewandte Chemie

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Seit seiner Entdeckung durch Christoph Hartmann und Victor Meyer im Jahr 1893 hat sich 2‐Iodoxybenzoesäure (IBX) zu einem geradezu ubiquitär einsetzbaren Oxidationsmittel entwickelt. Insbesondere in den vergangenen zehn Jahren wurde eine Vielzahl von Anwendungsmöglichkeiten beschrieben, die weit über die einfache Oxidation von Alkoholen hinausgehen. Dieser Aufsatz behandelt das Potenzial von IBX in der Synthese, wobei insbesondere unerwartete Reaktivitäten und moderne Anwendungen im Mittelpunkt der Diskussion stehen.

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“…The synthesis of an oligoannelated THF system with anti ‐fused rings making up a nonacyclic octaacetal has been reported (Figure 2). 14a…”

Section: Introductionmentioning

confidence: 99%

Diversity‐Oriented Synthesis of Enantiopure Furofurans from Carbohydrates: An Expedient Approach with Built‐in Michael Acceptor, Masked Aldehyde and Leaving Group in a Single Sugar Derivative

Manna

Pathak

2013

Eur J Org Chem

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A single sugar molecule containing three functional groups, namely a masked aldehyde, a Michael acceptor and a leaving group, reacts with a series of β‐dicarbonyl compounds and related reagents to form up to three new bonds and up to three new stereocenters. The configuration of the sugar derivative controls the diastereoselectivity in the formation of all the new bonds without a requirement for any external reagent for asymmetric induction. This “Chiral pool” based diversity‐oriented synthetic strategy has led to the formation of a series of furofurans based on different scaffolds and with appendage variations, and also to a hitherto unknown family of bicyclic 3,8‐dioxabicyclo[4.2.1]nonanes.

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anti-Oligoannelated THF Moieties: Synthesis via Push−Pull-Substituted Cyclopropanes

Cited by 99 publications

References 59 publications

2‐Iodoxybenzoic Acid—A Simple Oxidant with a Dazzling Array of Potential Applications

2‐Iodoxybenzoic Acid—A Simple Oxidant with a Dazzling Array of Potential Applications

2‐Iodoxybenzoesäure – ein einfaches Oxidationsmittel mit einer Vielfalt an Anwendungsmöglichkeiten

Diversity‐Oriented Synthesis of Enantiopure Furofurans from Carbohydrates: An Expedient Approach with Built‐in Michael Acceptor, Masked Aldehyde and Leaving Group in a Single Sugar Derivative

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