Mohr's salt catalyzed oxidation of aldehydes with <i>t</i>‐BuOOH

Chakraborty, Debashis; Majumder, Chandrima; Malik, Payal

doi:10.1002/aoc.1787

Cited by 14 publications

(7 citation statements)

References 60 publications

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“…Thereafter, a variety of oxidation methods, including Pinnick oxidation and Ag(I) oxidation, proved unsuitable. Oxidation methods described by Chakraborty and co-workers using tert -butyl hydroperoxide in combination with Fe(II) or Cu(II) salts gave excellent results when aldehyde 28 was used as a model system but resulted in only traces of carlactonic acid 3 when applied to aldehyde 30 . However, by this route we were able to synthesize “19-oxo-carlactone” 30 that has been hypothesized to be an intermediate in strigolactone biosynthesis but until now could not be synthesized successfully .…”

Section: Resultsmentioning

confidence: 99%

Synthetic Access to Noncanonical Strigolactones: Syntheses of Carlactonic Acid and Methyl Carlactonoate

2017

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Strigolactones are plant hormones regulating essential stages of a plant's development. Their low natural abundance combined with a low chemical stability significantly hampered the detailed investigation of their biological activity. Noncanonical strigolactones lack the fused tricyclic ABC-ring system commonly present in canonical-type strigolactones but feature an open-chain unit linking structurally diverse A-ring moieties to the butenolide D-ring. We herein present an efficient synthetic access to enantiomerically pure noncanonical strigolactones by a Stille cross-coupling approach to forge the central diene moiety and demonstrate this strategy by syntheses of natural products methyl carlactonoate and carlactonic acid. Furthermore, a synthetic access to deuterium-labeled analogues of these natural products has been developed.

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Section: Resultsmentioning

confidence: 99%

Synthetic Access to Noncanonical Strigolactones: Syntheses of Carlactonic Acid and Methyl Carlactonoate

2017

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“…33,34 It has been observed that the more substituted phenyl groups took longer time for completion of reaction. 35 Our protocol provides a milder and facile methodology for oxidation reaction that is useful for organic synthesis. a Reactions performed at 60 C and monitored using TLC until all the aldehyde was found to have been consumed.…”

Section: Resultsmentioning

confidence: 99%

Bio-derived CuO nanocatalyst for oxidation of aldehyde: a greener approach

et al. 2014

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“…Attempts to obtain the C-17 carboxylic acid were unsuccessful when 1 was treated with aqueous K2Cr2O7/H2SO4, NaClO2, 7 CuCl/t-BuOOH, 8 hypervalent iodine reagent 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (IBX), 9 or Mohr salt/(NH4)2Fe(SO4)2•6H2O]/t-BuOOH. 10 In most cases, aldehyde 1 remained unchanged and, in the treatment with K2Cr2O7/H2SO4, an intractable mixture of products was obtained.…”

Section: Scheme 1 Preparation Of Seco-oxacassane Derivatives 2-6 Starting From Natural Diterpenoidmentioning

confidence: 99%

Uncommon Reactivity of a Seco-Oxacassane Diterpenoid and Antiproliferative Activity of Some Derivatives

Torres-Valencia¹,

Hernández-Jiménez²,

De-la-Cruz-Martínez³

et al. 2021

HETEROCYCLES

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The main diterpenoid of Acacia schaffneri, 7,8-seco-7,8-oxacassa-13,15-dien-7-ol-17-al (1), has two aldehydes of which one is protected as a ε-lactol.The free aldehyde resisted to afford the carboxylic acid using reagents with different oxidative strength, although 1 gave oxime 2 when treated with hydroxylamine, β-hydroxyketone 3 after addition of acetone, aldo-ε-lactone 4 whereby only the lactol was oxidized when using Jones reagent, and epoxyformate 5 after Baeyer-Villiger treatment. Hydrolysis of 5 with NaHCO3 gave 6. Structures 2-6 followed from physical and spectral data including X-ray diffraction. All compounds showed antiproliferative activity similar to some chemotherapeutic drugs against C2C12, L929, SiHa, and MDA-MB-231 cell lines. RESULTS AND DISCUSSIONDiterpenoid 1 was obtained in adequate amounts for the preparation of 2-6 from the aerial parts of A.schaffneri. 1 Nucleophilic addition of hydroxylamine to 1 gave 2 in 66% yield, while aldol condensation of 1 with acetone in basic medium led to β-hydroxyketone 3 in 43% yield. The corresponding 1 H NMR spectra did not evidence both syn and anti oximes for 2, nor the absolute configuration (AC) of C-17 in the case of 3. However, the anti oxime geometry in 2 and the (17S) AC in 3 followed from the X-ray diffraction (XRD) studies detailed below. Although 3 was not the only expected condensation product, the γ,δ-unsaturated carbonyl compound could not be obtained even when using large excesses of acetone and NaOH.

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Mohr's salt catalyzed oxidation of aldehydes with t‐BuOOH

Cited by 14 publications

References 60 publications

Synthetic Access to Noncanonical Strigolactones: Syntheses of Carlactonic Acid and Methyl Carlactonoate

Synthetic Access to Noncanonical Strigolactones: Syntheses of Carlactonic Acid and Methyl Carlactonoate

Bio-derived CuO nanocatalyst for oxidation of aldehyde: a greener approach

Uncommon Reactivity of a Seco-Oxacassane Diterpenoid and Antiproliferative Activity of Some Derivatives

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