O,O-Silyl Group Migrations in Quinic Acid Derivatives: An Opportunity for Divergent Synthesis

Holmstedt, Suvi; Efimov, Alexander; Candeias, Nuno R.

doi:10.1021/acs.orglett.1c00755

Cited by 3 publications

(1 citation statement)

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“…Quinic acid which coexists frequently with shikimic acid in vascula plants commonly is an unique alicyclic organic acid of higher plants and a precursor of aromatic amino acid biosynthesis (Samimi et al, 2021;Holmstedt et al, 2021). Quinic acid with the multiple chiral centers structure is significantly and widely serves as a chiral raw material in stereo-organic synthesis to synthesize natural products and prepare new polymeric materials (Gabriel et al, 2008;Clifford et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

Quinic acid as a novel depressant for efficient flotation separation of scheelite from calcite

Huang¹,

Kuang²,

Yu³

et al. 2023

Physicochem. Probl. Miner. Process.

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There are difficulties to the conventional depressant for achieving separation of scheelite from calcite for the sake of their similar surface properties. The paper reported that a new depressant quinic acid (QA) was used for separating scheelite from calcite. The adsorption experiments, zeta potential experiment, contact angle, FTIR, XPS analysis and crystal chemistry analysis were utilized to known the depression mechanism of selectivity. The results showed that the recovery of calcite decreased drastically after QA added, whereas hardly influenced on scheelite. The tungsten concentrate could reach 66.24% WO3 grade and 89.46% recovery with 1.5×10-4 mol·L-1 QA at pH=9. The surface adsorption quantity of the QA on calcite was much greater than scheelite, which enhanced significantly the hydrophilicity of calcite surface. Due to its negative charge, QA could be adsorbed on the surface of calcite which had positive charge instead of that of scheelite with negative charge. Subsequently, free carboxyl groups of QA could chelated with Ca2+ species on the calcite surface to form stable chemical adsorption in order to prevent the Pb-BHA to form further adsorption on that, so there was no increase significantly on hydrophobicity. However, QA was obviously weak for adsorbing while Pb-BHA which could still be chemically adsorbed on scheelite surface of pre-treated with QA.

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Section: Introductionmentioning

confidence: 99%

Quinic acid as a novel depressant for efficient flotation separation of scheelite from calcite

Huang¹,

Kuang²,

Yu³

et al. 2023

Physicochem. Probl. Miner. Process.

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Deaminative bromination, chlorination, and iodination of primary amines

Xue¹,

Li²,

Tan³

et al. 2023

iScience

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Asymmetric Total Synthesis of the Rearranged Steroid Phomarol Enabled by a Biomimetic S_N2′ Cyclization

et al. 2023

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Phomarol is a structurally unusual 1(10 → 19)abeosteroid with a pseudo-symmetrical cycloheptene-1,3-diol motif, an aromatic B ring, and a densely functionalized tetrahydropyran ring. Herein, we report a 13-step synthesis of this natural product from inexpensive sitolactone by means of a convergent fragmentcoupling approach. Key transformations include a diastereoselective allylboration, a decarboxylative elimination, a Schonecker− Baran C−H hydroxylation, a biomimetic S N 2′ cyclization, and a late-stage 6π electrocyclization. Mechanistic studies indicate that the pivotal formation of the tetrahydropyran ring occurs via a silyl migration/intramolecular S N 2′ cyclization cascade rather than via an epoxide-opening process.

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O,O-Silyl Group Migrations in Quinic Acid Derivatives: An Opportunity for Divergent Synthesis

Cited by 3 publications

References 55 publications

Quinic acid as a novel depressant for efficient flotation separation of scheelite from calcite

Quinic acid as a novel depressant for efficient flotation separation of scheelite from calcite

Deaminative bromination, chlorination, and iodination of primary amines

Asymmetric Total Synthesis of the Rearranged Steroid Phomarol Enabled by a Biomimetic S_N2′ Cyclization

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O,O-Silyl Group Migrations in Quinic Acid Derivatives: An Opportunity for Divergent Synthesis

Cited by 3 publications

References 55 publications

Quinic acid as a novel depressant for efficient flotation separation of scheelite from calcite

Quinic acid as a novel depressant for efficient flotation separation of scheelite from calcite

Deaminative bromination, chlorination, and iodination of primary amines

Asymmetric Total Synthesis of the Rearranged Steroid Phomarol Enabled by a Biomimetic SN2′ Cyclization

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Product

Resources

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Asymmetric Total Synthesis of the Rearranged Steroid Phomarol Enabled by a Biomimetic S_N2′ Cyclization