IBX-Mediated Oxidation of Primary Alcohols and Aldehydes To Form Carboxylic Acids

Mazitschek, Ralph; Mülbaier, Marcel; Giannis, Athanassios

doi:10.1002/1521-3773(20021104)41:21<4059::aid-anie4059>3.0.co;2-r

Cited by 62 publications

(21 citation statements)

References 7 publications

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“…Finally, we found that oxidation of 2 with IBX in DMSO at 50 °C produced an intermediate aldehyde, which upon treatment with N -hydroxysuccinimide and further oxidation yielded an activated ester that was readily hydrolyzed under basic conditions to deliver (±)-actinophyllic acid ( 1 ) in 31% yield (Equation 3). 32 The spectral data for 1 matched that of a synthetic sample graciously provided by Professor Larry E. Overman. …”

Section: Resultsmentioning

confidence: 97%

Concise total synthesis of (±)-actinophyllic acid

et al. 2014

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A concise total synthesis of the complex indole alkaloid (±)-actinophyllic acid was accomplished by a sequence of reactions requiring only 10 steps from readily-available, known starting materials. The approach featured a Lewis acid-catalyzed cascade of reactions involving stabilized carbocations that delivered the tetracyclic core of the natural product in a single chemical operation. Optimal conversion of this key intermediate into (±)-actinophyllic acid required judicious selection of a protecting group strategy.

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Section: Resultsmentioning

confidence: 97%

Concise total synthesis of (±)-actinophyllic acid

et al. 2014

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“…First, the synthesis of 7 was accomplished through a former Sonogashira reaction with propargylic alcohol followed by a second Sonogashira coupling with 4‐ethynyl‐ N,N ‐dimethylaniline (Scheme ). Then, the one‐step oxidation of the hydroxymethylethynyl derivate 11 under the reaction conditions described by Mazitsche et al . successfully afforded the target compound in an overall yield of 66 %.…”

Section: Resultsmentioning

confidence: 99%

ABAB Phthalocyanines: Scaffolds for Building Unprecedented Donor-π-Acceptor Chromophores

et al. 2016

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Unique donor–π–acceptor phthalocyanines have been synthesized through the asymmetric functionalization of an ABAB phthalocyanine, crosswise functionalized with two iodine atoms through Pd‐catalyzed cross‐coupling reactions with adequate electron‐donor and electron‐acceptor moieties. These push–pull molecules have been optically and electrochemically characterized, and their ability to perform as chromophores for dye‐sensitized solar cells has been tested.

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“…[251][252][253] This reaction has been performed with an benzaldehyde derivative and IBX in the presence of N-hydroxysuccinimide as nucleophile. 254 However, this protocol was not successful in the synthesis of erythronolide A.…”

Section: Scheme 23mentioning

confidence: 99%